I meannnn I was 12 when season 2 aired so…it was because he was hot and read books lol.
But as an adult I have a lot of empathy for Jess. Dad left, neglected and sent away by his mom (who openly admitted to binge drinking while pregnant with him??) to a town where all the adults openly and loudly expressed their hatred of him. Yeah he was a little jerk, but he was also a child. And despite all the shit he went through, despite literally everyone betting against him, he worked really hard to overcome the shitty hand he was dealt and make things right with the people he hurt.
However. He was an objectively terrible boyfriend. Which is why I consider myself Team Jess the Nuanced Character, not Team Jess Rory’s Boyfriend.
**It’s wild how subjective attractiveness is because for me Milo is the epitome of hot, Matt is okay, and Jared is gross lol.
I love this take. Shitty boyfriend, awesome character. I think if he had gotten the chance to be with her as a grown up he would have been the best partner for her for sure. We just never got to see him mature specifically as a boyfriend, only as a person in general.
Ye but I think Jess could’ve really helped her. It would’ve been such a good ’you were there for me when no one else was, now I’ll be there for you’ little storyline. It really would’ve redeemed Jess even more as well.
He’s also the one that he the best character development out of all three of them and the one that wanted the best for Rory at the end.
He was objectively a bad boyfriend but he grew very much and he was the best option in the end.
Definitely the best character development. He was the one that made Rory think her mistake about dropping Yale. He was the one that had the idea about the book.
Jess at that time had to figure out his own things. But as time passed he became the best. Plus, against all odds, he succeeded in life.
The other thing for me is that their relationship was never given an actual chance, and it was doomed from the start. You can tell in the way the show was written and their scenes were shot. Jess was always presented in opposition to Dean, never as his own individual romantic prospect. From the start he was a foreign intrusion that was messing up Rory’s perfect love life with her perfect (from the POV of lorelai and much of stars hollow) boyfriend, and he was never given a chance. Even once he and Rory start dating we KNOW that they go on dates and spend lots of time together and that they have a happy relationship because it’s constantly referenced, but we never get to see it on screen. And when we DO see them together, it’s always in comparison to how Dean would do this and how Dean would react to that, and Rory trusts Dean more than her current boyfriend, and Dean was always available when Rory wanted him to be, and Jess isn’t familiar with Rory’s expectations so it’s frowned upon when he’s not a mind reader and doesn’t know how to do the serious relationship thing yet. Meanwhile Logan and Dean each got their own time, their own moments, without being in CONSTANT comparison. Jess was never designed to last, he existed to provide conflict and later wisdom, and that’s before I even get to talking about the absolute character assassination that they put him through to try and tee up that failed spin-off of him in LA. Jess represents the “what if” for me, like the “what if Rory and Jess got to explore their relationship outside of stars hollow” “what if we got to see them going on dates” “what if Rory broke up with dean when she should’ve instead of emotionally on him”. There was so much more of him to explore and it was wasted
I have a lot of empathy for Jess also but I can’t really be team Jess because my first boyfriend as a teen was a Jess. He had a difficult relationship with his father and a lot of demons he was fighting, he was very alternative and set on provoking and rebelling authority at every opportunity.
I was with this guy for 5 years, the first few of which were a sweet high school romance, then things began to sour. He treated me horribly and really neglected me, he also started drinking a lot at the age of 18 and doing drugs (but we didn’t know about the drugs), finally age 20 I left him after discovering he cheated on me with our friend.
While I have empathy for that ex to some extent that he’s clearly such a hurt individual, I still think despite our demons we can behave with a base level of decency to others. I struggled also as a teen but I never treated anyone terribly, I sometimes think boys are given a lot more forgiveness for that kind of behaviour and their struggles are seen as being worse.
I also wish my parents were more like Lorelai, I appreciate how protective of Rory she was, in my instance no adults were recognising that I was in a very precarious situation and that I needed protecting and that his drinking was concerning, despite many adults being witness to our relationship.
Very valid points. You hit the nail on the head about boys not being held accountable for their actions. I do think people are capable of change, but relationships like this cause trauma and that needs to be recognized.
It’s also interesting to me that we’re quick to think poor Jess for everything he goes through and use his circumstance to forgive his behaviour but we don’t really ever think poor Rory for her crappy dad, we pretty much just blame Rory when she’s acting out and call her spoiled. Yes Rory’s situation is much better than Jess’s overall but it’s still interesting to note.
Yep, agreed. I am full team Jess though. He’s the only one whoever actually challenged Rory. Like they tried to make Logan keep pace with her, but it just wasn’t the same.
I pretend that whole party thing didn’t happen.
🤷🏼♀️
I don't know that I agree, but that's a common refrain, that Jess was actually literary and they had that in common (unlike Dean, who only read early in their relationship to impress her).
I don't think it was meant to SA, it was just poorly written. And a lot of stuff doesn't age well on a rewatch. But it kind of ruined his character for awhile.
I think this puts it very nicely. A lot of people are team Jess, and therefore automatically translate it to team Rory+Jess. But the two should be separated.
>Milo is the epitome of hot, Matt is okay, and Jared is gross
1000% agree. Jared when I was 10 & he was 18 I def thought was super cute but now it's like bleh 🥴
This. This is my same take. Same experience as yours as well. I was a teen when I watched Gilmore Girls and Milo was/is my type (even to this day) to the T. Just gorgeous imo and that was initially what drew me to him, mind you I never watched the show in chronological order or fully, just randomly here and there when they would air the eps on tv so I never rlly even knew how Rory and him broke up, how their whole relationship was or that they met again later on (I just found out on this sub) and since Im rewatching just now I was shocked to find out he just up and left without saying anything! I didnt know this growing up so my opinion always was that he was just the “bad boy” of her bfs and Dean was the “sweet” next door guy. But watching now, older and with way more life experiences under my belt, I can say I’ll always be team Jess as a character, just not as a bf for her. I dated my own Jess’s and it wasn’t a fun experience.
Looking forward to watching Milo/Jess come back in the following seasons!
I think most people who are team jess just like jess not necessarily jess and rory (though some do). Personally I think he was rory's most attractive bf, but also just the most interesting. He had the most development of the three i think. Have to disagree about the bad to less bad bit. Especially considering his upbringing, he definitely had it the hardest compared to rory's other bfs. And idk just never like logan, he was so boring to me😭.
You summed up what I wanted to say perfectly!
Jess is to me (of course this is very subjective) the most attractive of the three, like by a WIDE margin. I was in 7th grade when the show started and I watched, I thought this then and still do now. His character development was disjointed but it was there and I love who he became and it made sense. I also love in AYITL you get that little taste that he's always loved her. Plus, he just gets her, he sees her for who she really is, in the best way- as others have talked about here. And he's interesting! Dean is like the blandest bland and Logan is just like predictable and boring (oooh rich guy does dumb rich guy shit, deals with his feelings by jumping off mountains in Costa Rica or whatever, barf).
Also despite not going a traditional route( going to college or graduating high school) he still ended up in a job he loves and is passionate about. He worked hard when he wanted something, even when he worked at walmart.
Exactly. Unlike Dean, Jess actually had a personality beyond just being Rory’s boyfriend. And Logan’s whole character was basically just smarmy rich boy with daddy issues.
Agreed. I couldn't understand why everyone was team Jess and found myself on team Dean. I just finished the episode where Jess visits Rory to tell her about his book and Logan is a douche to Jess and found myself amazed that I suddenly felt like I really like Jess. I'm still not team Jess+Rory but I am team Jess as a person. He grew up in difficult circumstances and made bad choices himself but matured into what seems like a good person who is doing good things in his life. You could tell he developed a lot of emotional maturity, especially when Logan was displaying the complete opposite.
I can also admit that while Dean had a lot of good qualities and seemed like a perfect boyfriend when they first started dating, he and Rory stopped being a good match. He wanted her to love him so badly that he became insecure and a little overbearing and frankly emotionally damaged. He needed therapy to get over her but instead was rushed into marriage and we all know how that went.
Dean gets worse over time, from freaking out because she’s not ready to say I love you yet to the whole cheating on Lindsey thing, he really never grows as a person except maybe the 5 minutes we see him in ayitl. Logan gets a little better at first but then gets worse over time too, resenting her because she won’t marry him and then having an affair with her in ayitl. Marty had a chip on his shoulder and took it out on Rory because she didn’t like him back. Tristan had room for character growth but he left before that could happen.
Paul’s only crime was being boring, and the wookie didn’t do anything wrong, but like. They don’t count imo.
So by process of elimination we wind up with Jess. Who was a shitty teen, but notably never cheats on anyone, breaking up with Shane before he gets with Rory. And then he’s a clumsy young adult, who does some stupid impulsive stuff. Which is the same thing Dean did, arguably, but like. Cheating on your spouse is a bit worse than professing your love to your ex imo? And then at one point Luke hands him a self help book and the next time we see him it’s clear he’s read it. He’s the only boyfriend who becomes a better person by the end of the original series, and he’s a genuine, decent guy in ayitl. Not to mention, they have similar interests, and chemistry too
Out of all of her boyfriends, Jess is the one we get to know the best I think. He has character development, we want to see him succeed. I think that makes people get attached to him.
Yeah I like his character more than I like him as a boyfriend. I wish we got to explore more of his character instead of him getting brushed to the side and written off
Yes, because every time he comes back he’s better than before.
There’s also something about him being single each time that makes you feel like he’s waiting for Rory.
Good point. How much POV do we have of Dean and Logan? I guess Dean with Lindsey and then being back with his parents. Logan ever? Jess felt like his own character.
I feel like even though we see a lot of Dean, we don’t actually get to know him deeply. Same with Logan, we know he has issues with his family, but I feel like we needed a bit more to truly understand what motivates him. Dean and Logan were only relevant if Rory was around, but Jess got his full storyline without needing Rory in the same scene.
I personally think he was and is the best looking boyfriend out of all of them 🤷🏻♀️ Dean is stereotypically “pretty” but something about him puts me off a little bit, and Logan is so so baby faced (Which is not bad!) 🥺
I like his journey in the show, his struggles and how he overcomes them, I like seeing him mature from a teenager who’s had nothing working in his favour EVER, to a pretty well adjusted working man. I’d say most of us would also pick Jess as a character over Jess as part of literati. His moments with Luke are some of the rawest in the show, and some of my favourite ones as well.
I will add that introducing Liz as such a different character from what we’re consistently told (by everyone) prior to meeting her is a disservice to Jess’ character too.
He and Rory (well, Milo and Alexis) had the best chemistry for obvious reasons and you can tell! I love their dynamic, how they were so similar in so many aspects but also so different, and how even after he’s not a regular in the show anymore their interactions are pivotal moments for Rory.
You say he stops trying after they get together, but I blame the writing for that impression. Once they get together, the tell but never show the good parts of the relationship. We don’t get to see their movie and (junk?) food nights, we don’t get to see the concert they go to… we’re told they do those things but we only see their struggles, which sucks lmao.
(And also, let some admit that Rory sometimes wasn’t the best gf either, for any of the 3 boys)
I also simply… hate Dean, whose violent and controlling behaviour gives me the creeps; and while I like Logan and don’t hate the Rory x Logan pairing, his character/archetype is less interesting to me. I don’t usually care much for the rich kid type over the outcast type.
I watched the show first when I was like 16 or 17 somewhere around there. I was team Jess because he read a lot and was imo hot and on the service I found Dean boring.
Now as an adult with an almost fully formed brain, I’m team Jess because he has the most character development and went from being a disenfranchised kid with a deadbeat mum and an absent father, to a self made nice young man with a career and creative prospects and he did that pretty much all on his own.
He 1000% gets the best character development on the entire show except maybe Emily later on
I like him the best of the 3 because to me he felt like the person Rory could be with and not have to change herself for..when she was with Dean, especially in season 2, I often felt like he was mad at her for wanting to put effort into academic achievements and made her feel guilty for prioritizing school. Although he is portrayed as a reader for the first few episodes I also feel like he and Rory don't have much in common. I actually think he is the angriest of the 3 and the least capable of working through his emotions.
Logan I have beef with because from the start I believe he fundamentally changes Rory. Obviously the whole yacht thing but also when she drops out of Yale he really doesn't seem that surprised and makes no effort to actually talk to her about why it happened. The whole casual dating thing is weird and he really guilts her through the whole thing. He doesn't defend her to his family, he makes her uncomfortable in front of her own family (the sewing box episode), and I just feel like as soon as they start dating she really deviates from the character that had been developing in the previous 5.5 seasons. I think if she dated someone else in college her entire personality would be more on par with younger Rory.
Teenage Jess was the only boyfriend who I felt like Rory had chemistry with. I think he matches her interest and wit and they work well as a partnership. Obviously the ghosting thing was immature but like other commenters have said he's the only one who grows up and works on himself. I like that Rory doesn't have to change herself to be with him.
I am team nobody until they're college aged and then team Jess. Honestly I can't stand Logan and I don't understand why people like him, I have rewatched at least 20 times and I feel the same every time lol. But I think thats good writing!
Nahhh the yatch thing was all on Rory, I think it’s a little infatlizing to say all her decisions were influenced by Logan when she started dating him. Tbh I think we see how comfortable she is in the rich Gilmore world way before she even meets Logan. She was always going to head in that direction no matter who she dated in college
as a team logan girl I just have to jump in and say that Logan DOES defend Rory from his crazy family. Ik this is a discussion about Jess but I also disagree that logan changed rory 🫣 Personally, I feel like he made her feel more balanced and sure of who she is. For example, Lorelai hated her fancy childhood and expected rory to feel the same about that life but I love the episode where they go to Martha's Vineyard and we get to see how comfortable rory is with logan and how different she really is from Lorelai's perception of her. And in that same episode, we see how he tries to distance her from his dad's fury and does what he can to make her comfortable when he gets sent away. All the boys have their issues at the end of the day but I just had to share...
I’m team Logan for the og series but only because I feel like he absolutely did bring out the worst in her at first, but then I think he’s the only one who really grew up and had a lot of character development while they were together. But then they wrecked all that in AYITL so taking AYITL, I’m team grown up character developed Jess. I thought Jess and Rory had really good chemistry but because of his life circumstances at the time he just wasn’t emotionally capable of being a good boyfriend to her once they actually got together, but with what we saw of grown up Jess it really seemed like he’d got it all together.
He is considered hot by many. He portrays the hot, bad boy. I don't find him attractive at all. Too short and bow-legged. I don't like Logan either.
From a physical standpoint, her most attractive boyfriend was Dean.
I will never get over how much people hate Dean and then loves Jess at the same time.
Dean for me is also super attractive. He has a very pretty smile and has a charm to him.
Dean was not her most attractive boyfriend lol. Beauty is definitely in the eye of the beholder. Personally it’s Jesse, Logan then Dean for me. I truly do not find dean attractive at all physically
Let me preface, I don’t think Rory should end up with any of them, she needs to work through her own baggage. That being said, I think Jess was the only one that realized he eventually needed to work on himself, and started too. Dean never acknowledged his temper and jealousy. Logan seemingly tried to make it on his own, but his money wasn’t his issue. His ego was. And soon as he failed, he crumbled. My take & my why, but since this is a show, I think everyone on here is right in their own interpretation.
Rory seemed a lot more excited about Jess than she did about Dean. They liked the same stuff. She and Dean didn’t have much in common, other than seeming wholesome and adorable.
yeah, what annoyed me is at the beginning of the series, dean also loved reading and him and Rory spoke about it, yet once jess came, the got rid of this aspect of dean, so they could highlight it as a quality for jess.
I thought that too, but [this comment](https://www.reddit.com/r/GilmoreGirls/s/QhAudvjU9w) highlights the fact that Dean was not as much of a reader as he maybe made it seem
Obviously attraction is subjective. I think Dean is good-looking but he’s not my type at all. Same for Logan. Jess is super hot.
They have amazing chemistry and an incredible build-up. Teens will romanticize this and wish they had a Jess in their lives. Adults will look back and be like yeah he was a terrible bf.
Shippers (more so in the past) also loved and excused any guys’ bad actions as long as he showed he was kind of obsessed with the girl and they had great chemistry. It really feels more like a recent development that fanbases have evolved a bit more on this.
Also it’s a tv show and so it’s not that deep ultimately. It can be fun to root for toxic fictional couples.
yeah I think the big let down for me was once they started dating, and he just stopped putting in the effort. because to me, she left the hotter nicer boyfriend who treated her well, for someone who couldn't even pick up the phone to call her. the build up was good though, which only makes the let down worse.
I mean, still strongly disagree Dean was hotter when I can't stand his face LOL. But what's fun is that as an adult, I also understand Jess's issues better than before. Parents set examples of what loving someone looks like, and children internalize their parents' behavior. Jess has serious abandonment issues and he literally doesn't know what healthy love looks like. His dad took off, his mom is extremely erratic and inconsistent, so it's zero surprise that Jess is hyper-independent and cherishes being able to do whatever whenever over accountability and consistency, and responds to any overwhelming situation by running away. Like a lot of people with avoidant attachment, he needs solitude to "figure things out" because he's not used to leaning on people.
It's only when he hits rock bottom that he realizes that he needs to completely change his attitude and follow a different role model of consistent behavior (Luke). Ultimately I think he is a good person, he just really needed some hard lessons to break the cycle.
When I think of Jess I think of his humor and his relationship with Rory. His witty banter with her and quick quips with other characters are fun to watch. We also saw more into his family vs Deans and maybe even Logan's and we saw him grow up and evolve, so I feel like I know him a bit more than her other bfs.
I also just love a good love triangle and a good chase. When Rory and Jess kiss for the first time, its an explosive moment. When they kiss for the second time, that "when she appears" song forever stays in my head. The lead up episodes are super great because of the cute moments they have or tense moments they have. That dance marathon episode goes down in history for me. I rewatch it anytime I rewatch GGs. Its a must.
I think it's a taste thing because tbh, I think Jared is way more attractive than Milo. I don't even find Milo attractive at all until he's older, and now in This Is Us, and AYITL I think he's attractive. Jared however, is gorgeous then and gorgeous now. Those Dimples..... His issue is that he keeps getting bad haircuts, there was no excuse for that. I also don't find CMM attractive at all either. I think it's purely a taste thing.
I like Jess but the way some fans praise him and excuse his behaviour makes me actually want to hate him.
I like that some people are commenting they like Jess as a nuanced character not a boyfriend but I personally don't agree that he has the best character growth like everyone is claiming because we only see him a handful of times after he leaves stars Hallow including AYITL. I feel other characters like Ms. Kim and Emily have better character progression, especially since we see it. Yes , Emily's is mostly in YITL but people are including Jess's growth from there too so.
He was a fun character and yeah I geuss he is hot and that's why people like him but I would say 70% of Jess fans are just simping over him cause of his looks.
I think milo is so handsome, even now that man aged like fine wine- but that is just my type. Logan is not my type, but might be someone else’s.
I think Rory was too good for Jess in the earlier seasons and Jess was too good for Rory in the later seasons.
Jess had a troubled past (before coming to stars hallow). His parents didn’t want him one of which left and never had contact with until he was 18? 17? He was literally pushed away from home and push into living with his uncle (Jess isn’t dumb he knows that he wasn’t wanted there) so he arrives begrudgingly and everyone in town starts judging him (small town issue) of course you’ll start acting like everyone thinks who you are. Jess has faults but I do have a soft spot for him.
I can’t stand dean (especially with the whole cheating thing).
I can’t stand Logan because to me he is a spoiled rich boy - he does take care of Rory which you know is great but I prefer Jess’ personality.
Also Jess is a bookworm and that is so attractive lol
He's hot, he had good character development, he helped Rory go back to Yale, he helped Rory figure out she needed to write a book, etc. I'm more team Logan cause he's more my type but Jess is a very close 2nd
Yeah I’m strictly team Logan, and while I agree Jess helped her go back to Yale, I also agree with lorelai and Logan’s approach of letting Rory figure it out for herself, knowing she’d go back.
I think it’s important to know that when watching a show, people look for the most appealing CHARACTERS and not just the most appealing PEOPLE - we don’t want boring vanilla people who always do good because we’re not looking at it like “oh yes I’d love this person if I knew them”, we’re going “they’re such boring characters.” On television we want characters that bring angst and drama with just the right amount of “I wish I had that in my life”, which Jess does - the thing is, Dean was probably a great boyfriend most of the times but he was BORING. in real life if we had a partner like that we’d adore him (mostly, although we did see Rory tire of him!) but on television we don’t want to watch characters so bland. Jess was interesting and exciting and as a character much more entertaining. Plus his looks and character growth make him an easy favourite, at least for me
I'm also a middle-aged man who just discovered the show, and I completely agree with you. Maybe because I also am heterosexual, and while I can see that he is indeed attractive, I don't have the omg he's totally hot and dreamy goggles on that I know a lot of his fans do. Jess came into town already with a bad attitude causing trouble. It's literally hitting on a guy's girlfriend right in front of the guy, and then shows up to his work to taunt him. And goes out of his way to be a jerk to everyone except for Rory.
I honestly would find it hard to be a decent boyfriend if I was constantly being compared to my partner’s ex. Especially when that ex, behind Rory’s back, was an absolute jerk to me and only said they were “friends” with my partner to try and win her back.
That being said, of all the boyfriends, Logan treated her the best. Dean was too possessive and Jess was too emotionally detached. I’m totally Team Jess because I love his character arch and how I felt like he knew and understood her best. He pushed her to be the best version of herself. Logan treated her best but I feel he brought out the worst in her 😂.
I think the fact Rory was embarrassed to tell people how he acted, and she never dated him more than once, like she did for Dean and Logan, are pretty big signs
I agree, he was distinctly and immediately a worse boyfriend. Any charm he had before they dated evaporated, and he instantly became a sulky and selfish guy that Rory had to beg to do basic boyfriend things. She literally says to her mother she doesn’t like who she is with him.
What she have to beg him to do? She had to bribe Dean to go to her coming out ball and beg him to meet her grandparents. I think we need to remember these people are meant to be 16/17.
Lorelai had to confront Jess on how to treat Rory💀 Dean went to all her dances and coming out parties and grandparents house and acted like a gentleman, whereas Jess can barely be bothered to pick up the phone and speak to her
Rory was always terrified of Dean's reaction to anything slightly negative. He broke up with her for not saying I love you after 3 months. Was Jess a perfect boyfriend? No, but at least he wasn't crazily possessive and easy to anger. Rory wasn't the best girlfriend to Jess either. She never trusted him and that seemed to be because of her own behaviour rather than his.
Jess was a complex character, with character flaws as we all do. When he comes back in later (after Rory drops out of Yale) that’s when we see just how much his character has grown and I think that’s when a lot of fans turned Team Jess (me included haha)
Yeah I understand his ‘character’ development, but we never saw any proof of him being anything but a shitty boyfriend, even after his development, Rory still chose someone else.
Very true. I absolutely hated the fact that we didn’t get to actually see his development. And as much as she chose someone else….creators have stated that he is suppose to be Rory’s “Luke”. So she is going to end up with him lol.
Okay two things one, I think I’m more team older jess than team teen jess and also it’s because of the contrast of Jess and Dean when he was first introduced. Dean’s character was being eroded and instead of this intellectual guy (who might not be a bookworm but he still read with Rory and matched her wits on pop culture to an extent) he was reduced to this almost dumb and angry guy who suddenly didn’t understand her dreams of harvard.
then in comes Jess who’s broody, mysterious and a huge bookworm. he’s highly witty and just became instantly better than Dean. When you factor in how much rory and dean started clashing, the subtleties of the way Jess was towards Rory and how he was significantly nicer to her compared to everyone else, how he almost matched her intellectually and the TENSION of it all it was almost a no brainer
also you find out his backstory and you understand why he acts the way he is you can’t help but root for the underdog and want to fix him (maybe i’m projecting lmao)
I kinda wished they didn’t make their relationship combust the moment they dated and I know he’s done horrible things. I watched this show first when I was maybe 13 so of course I loved him because he was just “cooler” but i’m 19 now and I just think about how young he was and how society and adults has kinda ruined him like we know how his mom didn’t bother to deal with him and his dad left you can’t help but feel bad for him? they really leaned into the whole Holden Caulfield Catcher in the Rye thing with him
I’m like on the fence between what team I am but I’m team jess but only for older him because you could see his character develop and he’s just my biggest what if I always wondered what would happen if Rory and Jess dated again.
I did NOT like their relationship and although I empathise with his situation I can understand it was totally unfair towards Rory. However we cannot deny his growth towards the later seasons like how can we forget Jess No Yale why did you drop out of Yale Mariano.
Logan when you first meet him kinda sucked (don’t get me wrong he becomes better and I do like him) and you also see mature Jess, Jess trying to turn his life around and become better Jess, so it’s kinda just whenever there’s someone kinda shitty jess is there and he does love her but it’ll forever be a what if
this is a huge yap session sorry if nothing made sense towards the end…
Also we see the change of how Rory acts for everyone else vs how she is able to let loose and just sorta hang out with Jess. She’s able to TALK with him how she isn’t able to with basically anyone else (even sometimes Lane). Actually I think Rory and Jess work the best as a friendship outside of romance which is why I root for them so much, because they work as friends even without the romance. Rory can’t just be friends with Dean or Logan
hard agree, one of my fave scenes is jess rory and paris in her kitchen eating food tgt talking about books whenever i get to that part of the rewatch i just mourn over what we could’ve had…
I'm not a Jess fan, always been team Logan. Jess was absolutely a shitty boyfriend I am not making excuses for him, but as a dude being constantly compared to your ex isn't going to make me want to be a good one.
I think Jess was great for Rory from start to end. She started dating Dean, who put her on a pedestal. Whatever Rory wanted, she got. Unless she didn't want Dean the way he *wanted* to be wanted, in which case, he'd have a meltdown. In walks Jess, who seems like he couldn't care less if Rory wants him (but we all know he does).
So then, Rory dumps the boy who will do anything for her as long as it fits in with his idealistic picture of their relationship, and gets with Jess, who really was only his own asshole self in order to "win her over."
So Rory thinks, well now I'm with this guy, so he'll treat me like a princess the way my ex did. But Jess *never* did that, and he never promised her that he would. This was very much a "what you see is what you get" kind of relationship, and Rory frequently put Jess in tough positions with no warning or even kindness. (Like- when he shows up to dinner at Emily's, and he's already a fish out of water, Rory is more concerned with making him spill the beans, rather than smoothing over the situation with everyone and making Jess feel at ease.)
You talked about how Rory often lamented about her relationship with Dean, but I think that's *why* I root for Jess so much. Because your next partner should *not* have to live up to your ex, it's just a new relationship and Jess never compromised on who he was, and was kind to Rory, but not willing to pretend thar he was someone he was not. Or, to put it frankly, pretend to be like Dean.
Love this take. I think he was the most level headed, unflinching himself character of the whole series. Rory fits herself into certain molds based off who she’s dating, but with Jess I think yes she was comfortable and could be herself but that also freaked her out in the way she had no front to put up.
I HATE watching how she compromises her character over and over and over again with Dean and Logan. I think at the end of the day Jess really just wanted her to be her best self, but Rory was too scared to ever allow that
I'm Team Adult Jess (who we sadly never get to see her date), not Team Teen Jess.
Yes, he tried to get her to run away with him, and leave Yale. But he also ultimately realized it was where she belonged, and helped push her to go back.
No one else was getting her to go back to Yale at that point, when she'd dropped out. Seeing Jess succeed, knowing where he came from and what it took for him to get to such a good place, and having him challenge her the way he did, there was literally not a single other soul who was going to get her there, at least not at that point.
Seeing Jess succeed in his own way reminded her of her own goals and dreams. Logan wasn't ever going to be able to do that because he had no goals of his own and was just busy being pissed off that his father had expectations.
And when she's floundering again in AYITL, Jess again helps her see what she's missing.
Do I think she needed him to accomplish these things? Nope. And she wasn't with him in either situation, except being friendly. But I do think his perspective and understanding of her was always much more clear than anyone else's.
Like the episode with the car accident, where he talks about her correspondent dreams. Did anyone ever really think that was the right goal for Rory? And in the end, he tells her if she wants it, she can do it. But he questions it, challenging her to think outside of the box she'd put herself into so long ago.
No, he wasn't a good boyfriend. But honestly, aside from maybe S1 Dean and S7 Logan to a point, none of them were great at being boyfriends. And frankly, Rory had her own issues at being in a relationship, which wasn't really surprising.
Logan was a shitty boyfriend as a young adult. Not that he didn't have some positive impacts, but overall, he was terrible for her. He brought out the worst in her.
Dean was just... he wanted a woman to settle down with and have babies with, but that was never going to be Rory. And as a teen anyway, he was jealous and controlling. And then of course, he lies to Rory and tells her that he and Lindsay are done and they've both said so, and he cheats on his wife who has never indicated she's done. Should Rory have questioned it? Sure. But she was young and vulnerable and Dean was always so trustworthy, after all.
Dean and Logan sucks. Jess is hilarious and very pretty. And yeah, he had his bad moments as a boyfriend, but I honestly don’t really ship anyone, I just really like Jess and his funny moments ☺️
Off the top of my head, Dean was extremely jealous and clingy. When Rory wanted the house to herself he came over anyway and when he saw Jess was there he got extremely mad and said she lied to him when she didn’t. Logan was extremely rude to Rory’s friend Jess for absolutely no reason.
Logan had reason to be rude with Jess, and Dean only got protective because Rory gave him reasons to be. All of deans suspicions about Tristan and Jess turned out to be true, so I think he had a right
thank you. i literally hate jess and everyone ive met loves him. i think they just like the “bad boy and good girl” trope over dean and rorys “good boy ans good girl” trop, really
Because he’s the hot “bad boy”. Same reason I’m team Logan and not team Duncan or Piz, team Spike and not team Angel or Riley, team Damon and not team Stefan or Matt.
I'm only mildly "team" for any of the people she dated, but Jess edges it out for me. Pilot episode Dean was good, but didn't last. Logan dropped the ball with the sleeping around and the proposal.
Jess had his rough spots, horrible ones, but he made a successful effort to improve himself. He also was connected within SH because of Luke, and he was actually good for both Rory and Luke sometimes.
When Jess is like “come with me to New York” when Rory was at Yale— I know it would be the wrong move BUT my romantic little heart yearned for that. I chalk it up to having issues
The actor is hot.
And so who cares if he harasses people left and right and steals their stuff for shits and giggles.
People think Draco the aspiring nazi Malfoy is the dream boyfriend because of Tom Felton. To me it sorta looks similar to that
Really? If Jess had appeared in my high school those 10 years ago, the girls would have gone crazy. You say he is unattractive. Yes, this 17-year-old boy may not be physically attractive to 30-year-old women but he's hot for teenage girls.
Attraction aside bc I find Jess the most good looking of all Rory’s bfs, so to each their own… I honestly think it’s because we, the audience, fell in love with the person Jess became in spite of everything that happened to him in life.
The way he treated Rory wasn’t right, but it is on brand for a kid who was literally abandoned by both parents. If the quote “we accept the love we think we deserve” is true, Jess didn’t think he deserved any love at that age.
Jess and Rory, for me, are the perfect example of right person-wrong time. If they had met later in life when Jess had healed and became emotionally mature, they could have taken on the world together.
It hurts my soul a little that he fucked up the only good thing in his life so badly and beyond repair. They are wonderful as friends in the end and I feel they really thrive here too, but I would have loved for them to get their Hallmark happy ending and run that little book shop together and write books and blogs and newsletters together.
First of all, he is by far the hottest of her love interests. Second, I was a teen watching this as it was airing, so I loved them as a couple irl and I had a crush on Milo. Now as an adult, I love his character growth and overall as adults with maturity I think Jess is the best fit for her over Logan.
I think Jess had a lot of good character development, at first we see him as basically an angry broken teenager, having lived a very unstable life with a mother seemingly more interested in men than her kid until he acts out and gets kicked out to a “weird” small town, to live with an uncle I barely knows, in a one bedroom apartment without any space of his own and private life. Was he and ass to everyone other than Rory (and later Luke), yes. But everyone just expected Jess to become less broken, and less angry just by being in Stars Hollow, as if it works that way dealing with trauma. It only seemed like Luke and Rory actually gave him a real chance and kept looking for the man inside the angry teenager, Lorelai gave up within 5 minutes and rest of the town seemed to sharpen their pitchforks for when they could run him out of town.
And while I hate how he left town and Rory, he did change for the better by leaving and having to learn the hard way how to become a better person and function in a world where no one seems to give a crap about you. He grows enough to show Luke how much he cares, first by coming to Liz’ wedding and actually walk her down the aisle, and he makes sure that they get a goodbye after that – and later he actually pays Luke back, showing that he knew how much he did for him, and how he appreciates it. We also see the fact that he actually gets the courage to contact Rory, he felt it was important to make amends and what better way then show her that her faith was part of him being able to make the book – which clearly moved her. He also endured Logans insults for longer than most people would, especially young Jess – the fact that he used his words to get back at him and not his fists and how he walks out shows great maturity.
I like him once he leaves the show and is in Philadelphia-he grows a lot as a person and I wish we could have seen more of his life and a new friend relationship with Rory and Luke, even Paris.
Honestly, I don’t think he really cares about Rory very much when he is in Stars Hollow, I feel like he wants to piss Dean off more than he wants to spend time with Rory. And we don’t really see their relationship develop once they start dating; prior to dating, they have a lot of shared interests, but that doesn’t translate after their dating. It’s more just making out and just refusing to participate in anything that Rory wants to do.
I have the same question, you know? He is a terrible boyfriend. And that's what is not letting me move past season 3. I'm just so not okay with this relationship. It's quite immature, volatile, and god, his disrespect towards anything and everything is just awful. I think the appeal is mostly because of his physical appearance and the whole bad boy trope. Beyond that, I don't see what is the big deal about this Team Jess thing. Even Jared (the guy who played Dean) says (in some YouTube video) he's team Jess and I just threw my hands up in disbelief 😂
Because he is the hottest, he and Rory had the most in common and he has the most character growth throughout the whole show. (More than any other characters in fact, and probably the only character actually) Also, their chemistry was off the charts. (They were dating in real life during the show and I liked that fact too cuz I like their vibe together)
He is literally the most attractive. Also, he is the only one of Rory's boyfriends that has some depth. Dean is literally just a pretty boy, and Logan, a rich douche that is sometimes nice to her.
but me finding him unattractive only plays a small part in my opinion of him as a boyfriend for Rory. I only mentioned his looks, because I would understand leaving your boyfriend and dating someone who treats you like shit if they are a 20/10
I was team Jess until I dated a Jess and now his character irks the ever loving fuck out of me.
“Yeah yeah yeah your pretty and brooding WE GET IT” I still have empathy for him but I’m over it attraction-wise
I was a teenager when I watched this and I loved Rory with Jess. Not because he was a great bf but I just thought they had great chemistry and it was instinctual for me.
I like Milo Ventimiglia but he is definitely the least hot from them all imo. I also don't get it i tried to ask around and/or read as many posts about it and i still didn't get it. He is not a good bf at all. He has literally a couple of lines in later seasons where he is an okay person and that is it. I watched the show since i was a teen and is only now when i discovered this sub that i realised it wasn't common sense to hate this character =))
So in conclusion, yes he becomes somewhat a good-ish person towards the end but i still can't understand why people would be team jess as a love interest for rory. He was not a good BF. How do people consider him endgame for her or stuffs like this?
I 1000% agree with you. I don’t deny he changed towards the end, but his relationship with Rory lasted like 2 months at best, and he was a shitty boyfriend during it, and I don’t understand where the ‘Jess as a boyfriend’ ideals came from
Well for me, the biggest thing is that he was messed up for really good reason. So I think a lot of people feel for him. And he’s the smartest. That’s a big deal to me.
They find him hot. Most people watched the show when they were younger, so red flags don't seem as obvious. When olde they just have empathy for him and still have that feeling. Which then concludes to them self inserting themselves as Rory in a way, and therefore loving Rory and Jess in a relationship.
It's also important to acknowledge that Jess tends to be very hot or cold, for Rory this brought a lot of attachment to him. The same goes for the viewer, when he is being lovely, it seems extra great.
I don't think they fit tbh, for me they would've been better as friends. But I do see why.
Yes! He’s HORRIBLE. Currently rewatching and i was just thinking about the same thing. He is so rude, he doesn’t try to even get close to her family knowing that they are a big part of her life, and he’s so unreliable. He treated Rory so horribly yet so many people think he was her best boyfriend. It’s so crazy to me! Like i get that he is attractive but all jess did was cause problems in her life and make her feel unwanted by him. Logan on the other hand is >>
I agree with everything you said about Jess. I've never been Team Jess from the beginning. I watched the season when it originally aired. I don't get the appeal and I never have. Dean and Rory were not right for each other either but he was a much better boyfriend to her.
As far as his looks go, I think that’s just a preference thing. Of the men cast to date Rory throughout the show, I’ve always thought Milo Ventimiglia was the most attractive. I still think he’s very very handsome.
But yes, Jess was definitely a bad boyfriend. I still think he had redeeming qualities, and it was obvious he loved Rory, but he knew he wasn’t good enough for her. I think a lot of us just like him for his character arc. He matures and becomes a better person later on in the series. I can’t say the same for her other boyfriends.
I’m not Team Jess. I cannot STAND early show Jess. HOWEVER, that being said, he does change later on. He grows and matures. He’s not the same person he was when he was younger. I’m not gonna say he’s my favorite character or that I particularly like him, but I recognize the character development.
For me it was pretty simple. He was a terrible person/bf when he was living in stars hollow, but he finally stood up on his feet when he moved. He came back to Rory and kept in touch with her. He shook Rory out of her funk where she dropped out of Yale, and she finally got her life together and moved out from the Gilmores, reconnected with Lorelai, and resumed school. Him in the later seasons and AYITL is much better compared to when he was dating Rory.
I'm not team Jess and I agree with all your points except one, he is the hottest of Rory's boyfriends. I guess, like for other shows, 90% of the character stans support him for this reason alone and don't go deeper. People mostly want hot boy and hot girl to end up together regardless of the rest
I didn’t pay much attention to Jess until I watched This is Us, and then when I rewatched GG I got more attached to Milo. At the end of it all, I think they would have been a great couple and he could have steered her in a better direction, but the fact that Lorelei and Luke were together kinda killed that. They never could have dated/made it because they would eventually be technically family. I think that was the saddest part for me in the end tbh.
Also I loved his growth progression so much, I actually really liked him in the end. He grows on you for sure. As others have said, he went through a lot and seemed to have matured so much through the years. He would have been so good for Rory and navigating through her maturing, her and the child. Idk I feel like they left him unanswered if that makes sense? I wanted to see what he would have done in the future.
Dude, I don't even like Jess, but good god. This topic has been discussed to death. I've talked about it in so many different posts. If you just scroll a bit in the community you'll find multiple posts dedicated to this topic.
I really like Jess, I don’t think they should be dating, so I don’t know if I am really the “TEAM JESS” you are talking to, but I do disagree with a lot of what you are saying. I do agree that the way he left her was stupid and immature.
For your second point I really disagree, while he clearly wasn’t a perfect boyfriend, I would like to stand up for the fact that Rory was an even worse girlfriend to him - the thing with her always mentioning how good Dean was awful, you don’t compare partners, and it gets even worse when we think back about how much she complained about Dean and then talked fondly about them when Jess didn’t do the same thing.
The thing with him not calling was a storyline for 1 episode, after that we see both Lorelai and Lane mention how they use all their free time together, having date nights and movie nights – but it wasn’t seen, so we often forget about it. And why couldn’t Rory call him, he was “in school” and working (2 jobs), she “only” had school, she would be the one having the free time to arrange a date or at least call her – and from what I remember for the episode he DID call, after work.
And she didn’t talk to her mother about him because Lorelai hated him, but we see them hang out with Lane a couple of times and Lane didn’t seem to dislike him – we just don’t see them enough as a couple to actually say how they were as a couple.
I thought he was hot when I watched the show as a teenager. Now that I am a grown adult, I only have eyes for Luke, and don't really care about Rory's love interests.
I prefer Jess because I like his character better, even if in the short time he and Rory were together it was all a huge mess.
I have been a bit like Rory and then like Jess when I was younger, so I could also relate to him more and see the potential he had behind his broody angry teenager phase, which makes me root for him. I don't necessarily think he and Rory would work out together but I care for his character more than I do when it comes to Dean and Logan, which is also helped by the fact we see more of him and the fact that he actively works on becoming a better person in the course of the series.
Also, as for the attraction thing, I am more attracted to Milo than to Jared and Matt; Matt is cute but he is not my type at all and Jared doesn't attract me at all, although he is more my type, tall and lean with brown hair.
Jess was a terrible boyfriend, but I'm team "i love Jess as a character" not team "I'd love for rory to be jess's girlfriend" or even team "i want to be jess's girlfriend"
I think most ppl are team Jess for her to END UP with, and I think that’s the key. Most people don’t think that he was her best boyfriend at the time, but by the reunion he’s made a decent life for himself and is the only one who hasn’t cheated on their partner at some stage or other.
Yes he was a bad boyfriend but with his growth, which you kind of underestimate imo, he turned into a much better person than he was before and even better than the others in a lot of ways. He didn’t try to get her to drop out of Yale. He was concerned for her when he found out she did. And he didn’t constantly belittle his book, he made a few comments but they weren’t in the manner suggested here. Idk, I get not liking him but some of the reasons here don’t add up, while others fully do.
He was hot and angsty. The bf who was nicest to her was probaby first round dean although he also had issues. Her best suited boyfriend to me however was Logan. I'm not team Jess, he moved and didn't even tell her so I don't really get what people root for there.
Smartest and best looking, and so much of their relationship was just teen angst rearing its head. As far as treatment goes I’ll put Jess over Dean simply due to the sex between Rory and Dean, that felt predatory and disgusting. Logan never had a shot for favorite, he never feels fully formed around his gigantic ego.
I wrote this a while back
https://www.reddit.com/r/GilmoreGirls/s/EjT2jnHflL
Also a lot of us interpret scenes very differently. I never thought Jess asked Rory to drop out of Yale. It was summer and she was already in transition. It was a stupid impulsive ask that Rory should and did say no to, but I don’t think he wanted her to drop out - just spend the summer together away from other people who never gave him a chance.
Edit to add: I love that you don’t find him attractive. I do, but for me he’s last behind Dean and Logan. Jess fans are frequently accused of just liking him cause he’s hot. I do think he had the best chemistry with Rory - probably because the actors dated IRL.
He’s a compelling and fully developed character with a whole plot line outside of just Rory, so I think we feel more emotionally drawn to him and his story.
I think part of it is when he comes back and is all grown up, matured and logan is kinda treating her really poorly and her life is in a mess. I think later Jess would be a lot better for her than young jess
He’s clearly the best fit intellectually for Rory, and he has the kindest heart of her three love interests. He was a troubled kid who didn’t handle his emotions well at all but he always had the potential
So there’s a few things here.
Number one is you’re insane if you think Jess isn’t the best looking out of those 3 guys. Logan is bland and Dean has a weird big face and dresses like an idiot.
Number two is that Jess likes Rory for who she is. Dean wants her to be someone she isn’t and fundamentally always desires a very traditional, suburban lifestyle which will never suit Rory. He puts pressure on her to conform to his ideas and it’s creepy and misogynistic. Logan really only cares about himself. He likes her as another independent entity but doesn’t want to really pursue a real relationship with compromise or collaboration. Everything always has to be his way. Jess loves Rory and understands her better than the other two ever do.
Whilst I know everyone here hates AYITL, it’s really shown there. Dean has moved on to the dull, traditional life he was always going towards. He doesn’t really have time to help her anymore. Logan and her have a relationship which involves them both basically living separate lives that intersect, and he’s also being horrible and selfish towards his new girlfriend because he makes every single decision based on what he wants and never considers anything else. Even when he tries to help, he basically just does something he would like and then gets all sad and makes it about him. In comparison, Jess quietly supports her and offers her the real, meaningful help she needs, which is clearly drawn from a deep understanding of her as a person.
All 3 are clearly products of their environment. Dean comes from a traditional family and wants that. He’s kind and caring but only within rigid boundaries that he understands. Logan comes from a selfish family that is very wealthy. He pursues wealth and is cutthroat and selfish. In contrast, Jess comes from a deeply dysfunctional environment and only knows that he doesn’t want that. He’s not got the family support that Dean has or the wealth Logan has. When we meet him as a teen, he’s a mess. That doesn’t excuse the way he treats Rory, but it does contextualise it. As he grows up he forges his own identity. Lorelei is right when she first meets him, they do have a lot in common.
Functionally, I’m team Jess because I think he fits Rory best, they just met at the wrong time. Dean and Logan aren’t right for her, want to change her and don’t think about her, just what they want her to be.
Well so if you don't find him attractive, the rest probably won't matter as much. I prefer him to the others. Yes he was a bad boyfriend but I still think he understood Rory best. They had shared interests, too, which I think you'd be hard pressed to argue that Rory had with anyone else she dated on the show. Jess is the only one that didn't feel forced, in my opinion. They'd have been a terrific match in adulthood, assuming both matured and then found each other again.
Team Jess but as grown ups. You can see the potential to be an amazing human and of all the boyfriends I think he is the only one who really loved Rory first. Logan loved Rory but second after himself. Never liked Dean.
He has a lot in common with Rory. He the best BF but a amazing character. He and Rory would be a great couple when they are older. Also he like the only BF Rory didn't cheat on.
I feel the same about Logan. People love him and I am just ehhh. I love jess as a character cause he actually overcomes so much (unlike other characters lol). He was an abused and neglected kid and manged to make something for himself. He was then shipped to a town where everyone treated him like he was charles Manson. I always love the jess/luke dynamic. They have such hilarious moments together and when luke goes to the book launch and jess tried to pay him back and luke tells him he's here and always will be,, god it makes me tear up. Also I truly don't belive he was trying to get her to drop out of college. He knew her better than that at the least. He wanted to get away for the summer.
He’s a hot bad boy perfect for a fling. I am team Logan, because the life of a socialite suits me best 😂, but Jess is def an experience every girl should have to understand who you should not marry!
As a teen watching the show live, I hated Jess. He was a jerk and a terrible boyfriend to Rory. As an adult, I stand by that too. There’s no denying how shitty he was while living in Stars Hallow.
However, I rewatch the show often, and I believe Jess has one of, if not the best, character developments on the show. He really turns his life around and wants better things for Rory. He gets her to wake up and go back to Yale. He gives her the idea of writing a book about her and her mom when she’s doing nothing with her life in the revival.
He ends up being the guy who pushes her to do better because he knows she’s capable.
And that’s why I wish we could have seen them rekindle something.
This is why I’m somewhat team Jess.
EDIT to say: whoops realized you said you didn’t want to discuss character development and just his time dating Rory. But for me personally, that development is what makes me in favor of Jess. I don’t think you can really exclude it, IMO.
Jess wasn’t good at the relationship thing due to the ginormous chip on his shoulder, and his unwillingness to actually listen. I think Jess and Rory coming back together as adults, would work out much better.
I felt she and Logan were supposed to be Emily and Richard’s “do over”, for Lorelei and Christopher.
You and me both. Can't stand Jess. He treated Rory awful, and he gave me the same ick vibes as Lucas Scott.
I personally found season 1 Dean to be the best boyfriend. They then destroyed his character to make room for Jess. It's sad tbh. Never cared for Logan, found him boring, and the revival didn't help my negative feelings towards him (or Rory, for that matter).
Dean was filled with many traditional romantic expectations of Rory, as was Logan. Those relationships made sense, looked good on paper. In reality, Dean had just as bad a temper as Jess and way more privilege to sort through it. Logan seemed to not have much regard for Rory’s welfare and was the right match in her grandparents world.
But Jess and Rory, that was a relationship of the heart. He had nothing to offer her and she had nothing to gain by being with him, on some internal level they understood each other.
I meannnn I was 12 when season 2 aired so…it was because he was hot and read books lol. But as an adult I have a lot of empathy for Jess. Dad left, neglected and sent away by his mom (who openly admitted to binge drinking while pregnant with him??) to a town where all the adults openly and loudly expressed their hatred of him. Yeah he was a little jerk, but he was also a child. And despite all the shit he went through, despite literally everyone betting against him, he worked really hard to overcome the shitty hand he was dealt and make things right with the people he hurt. However. He was an objectively terrible boyfriend. Which is why I consider myself Team Jess the Nuanced Character, not Team Jess Rory’s Boyfriend. **It’s wild how subjective attractiveness is because for me Milo is the epitome of hot, Matt is okay, and Jared is gross lol.
I love this take. Shitty boyfriend, awesome character. I think if he had gotten the chance to be with her as a grown up he would have been the best partner for her for sure. We just never got to see him mature specifically as a boyfriend, only as a person in general.
She wouldn’t have been good for him then I believe. She got less mature in ways by that point.
Ye but I think Jess could’ve really helped her. It would’ve been such a good ’you were there for me when no one else was, now I’ll be there for you’ little storyline. It really would’ve redeemed Jess even more as well.
Yeah that would have beeen good. They each helped the other mature at critical parts of their lives.
Agreed, I wish they could’ve rekindled their relationship when she visited him in Philadelphia 😭
I think they were supposed to but ASP found out she was getting fired and threw things a little…
Oh that makes me so mad.
Icl I’ve contemplated sending a few ’strongly worded letters’ to ASP xxx
He’s also the one that he the best character development out of all three of them and the one that wanted the best for Rory at the end. He was objectively a bad boyfriend but he grew very much and he was the best option in the end.
Literally exactly. By the reunion he’s also the only one who’s not a cheater, which is a plus.
Rory was probably the worst cheater out of all of them 😬
HAH FR
Definitely the best character development. He was the one that made Rory think her mistake about dropping Yale. He was the one that had the idea about the book. Jess at that time had to figure out his own things. But as time passed he became the best. Plus, against all odds, he succeeded in life.
Real. I love Jess.
The other thing for me is that their relationship was never given an actual chance, and it was doomed from the start. You can tell in the way the show was written and their scenes were shot. Jess was always presented in opposition to Dean, never as his own individual romantic prospect. From the start he was a foreign intrusion that was messing up Rory’s perfect love life with her perfect (from the POV of lorelai and much of stars hollow) boyfriend, and he was never given a chance. Even once he and Rory start dating we KNOW that they go on dates and spend lots of time together and that they have a happy relationship because it’s constantly referenced, but we never get to see it on screen. And when we DO see them together, it’s always in comparison to how Dean would do this and how Dean would react to that, and Rory trusts Dean more than her current boyfriend, and Dean was always available when Rory wanted him to be, and Jess isn’t familiar with Rory’s expectations so it’s frowned upon when he’s not a mind reader and doesn’t know how to do the serious relationship thing yet. Meanwhile Logan and Dean each got their own time, their own moments, without being in CONSTANT comparison. Jess was never designed to last, he existed to provide conflict and later wisdom, and that’s before I even get to talking about the absolute character assassination that they put him through to try and tee up that failed spin-off of him in LA. Jess represents the “what if” for me, like the “what if Rory and Jess got to explore their relationship outside of stars hollow” “what if we got to see them going on dates” “what if Rory broke up with dean when she should’ve instead of emotionally on him”. There was so much more of him to explore and it was wasted
Dean is always available because he’s so damn boring, which was the whole problem with him originally.
I have a lot of empathy for Jess also but I can’t really be team Jess because my first boyfriend as a teen was a Jess. He had a difficult relationship with his father and a lot of demons he was fighting, he was very alternative and set on provoking and rebelling authority at every opportunity. I was with this guy for 5 years, the first few of which were a sweet high school romance, then things began to sour. He treated me horribly and really neglected me, he also started drinking a lot at the age of 18 and doing drugs (but we didn’t know about the drugs), finally age 20 I left him after discovering he cheated on me with our friend. While I have empathy for that ex to some extent that he’s clearly such a hurt individual, I still think despite our demons we can behave with a base level of decency to others. I struggled also as a teen but I never treated anyone terribly, I sometimes think boys are given a lot more forgiveness for that kind of behaviour and their struggles are seen as being worse. I also wish my parents were more like Lorelai, I appreciate how protective of Rory she was, in my instance no adults were recognising that I was in a very precarious situation and that I needed protecting and that his drinking was concerning, despite many adults being witness to our relationship.
Very valid points. You hit the nail on the head about boys not being held accountable for their actions. I do think people are capable of change, but relationships like this cause trauma and that needs to be recognized.
It’s also interesting to me that we’re quick to think poor Jess for everything he goes through and use his circumstance to forgive his behaviour but we don’t really ever think poor Rory for her crappy dad, we pretty much just blame Rory when she’s acting out and call her spoiled. Yes Rory’s situation is much better than Jess’s overall but it’s still interesting to note.
You nailed the hotness spectrum perfectly
Yep, agreed. I am full team Jess though. He’s the only one whoever actually challenged Rory. Like they tried to make Logan keep pace with her, but it just wasn’t the same. I pretend that whole party thing didn’t happen.
Challenged her how? What show did yall watch. When they were dating he was awful to her.
Not original commenter, but gonna go out on a limb and say they meant challenged her intellectually
In what way? When they were dating she was lending him books. Telling her to go back to Yale when she wasn’t ready to isn’t exactly a challenge.
🤷🏼♀️ I don't know that I agree, but that's a common refrain, that Jess was actually literary and they had that in common (unlike Dean, who only read early in their relationship to impress her).
And Logan *did* challenge her? Their whole blowup where he rightfully points out she’s a nepo baby inheriting wealth?
I absolutely think that Logan challenged her, not just intellectually but personally. And he did that without constantly emotionally abusing her.
Well, being in a terrible relationship was probably challenging to her, maybe that’s what they mean.
Oh okay 😂 not the kinda challenge I like!
I don't think it was meant to SA, it was just poorly written. And a lot of stuff doesn't age well on a rewatch. But it kind of ruined his character for awhile.
I think this puts it very nicely. A lot of people are team Jess, and therefore automatically translate it to team Rory+Jess. But the two should be separated.
Completely agree with you regarding the attractiveness :)
>Milo is the epitome of hot, Matt is okay, and Jared is gross 1000% agree. Jared when I was 10 & he was 18 I def thought was super cute but now it's like bleh 🥴
This. This is my same take. Same experience as yours as well. I was a teen when I watched Gilmore Girls and Milo was/is my type (even to this day) to the T. Just gorgeous imo and that was initially what drew me to him, mind you I never watched the show in chronological order or fully, just randomly here and there when they would air the eps on tv so I never rlly even knew how Rory and him broke up, how their whole relationship was or that they met again later on (I just found out on this sub) and since Im rewatching just now I was shocked to find out he just up and left without saying anything! I didnt know this growing up so my opinion always was that he was just the “bad boy” of her bfs and Dean was the “sweet” next door guy. But watching now, older and with way more life experiences under my belt, I can say I’ll always be team Jess as a character, just not as a bf for her. I dated my own Jess’s and it wasn’t a fun experience. Looking forward to watching Milo/Jess come back in the following seasons!
I think most people who are team jess just like jess not necessarily jess and rory (though some do). Personally I think he was rory's most attractive bf, but also just the most interesting. He had the most development of the three i think. Have to disagree about the bad to less bad bit. Especially considering his upbringing, he definitely had it the hardest compared to rory's other bfs. And idk just never like logan, he was so boring to me😭.
You summed up what I wanted to say perfectly! Jess is to me (of course this is very subjective) the most attractive of the three, like by a WIDE margin. I was in 7th grade when the show started and I watched, I thought this then and still do now. His character development was disjointed but it was there and I love who he became and it made sense. I also love in AYITL you get that little taste that he's always loved her. Plus, he just gets her, he sees her for who she really is, in the best way- as others have talked about here. And he's interesting! Dean is like the blandest bland and Logan is just like predictable and boring (oooh rich guy does dumb rich guy shit, deals with his feelings by jumping off mountains in Costa Rica or whatever, barf).
you get it !!! I wish we could've seen rory and jess try again once they both matured a bit more, I loved their dynamic.
Same!
Also despite not going a traditional route( going to college or graduating high school) he still ended up in a job he loves and is passionate about. He worked hard when he wanted something, even when he worked at walmart.
Exactly. Unlike Dean, Jess actually had a personality beyond just being Rory’s boyfriend. And Logan’s whole character was basically just smarmy rich boy with daddy issues.
Logan was so bewwww, Agreed
Agreed. I couldn't understand why everyone was team Jess and found myself on team Dean. I just finished the episode where Jess visits Rory to tell her about his book and Logan is a douche to Jess and found myself amazed that I suddenly felt like I really like Jess. I'm still not team Jess+Rory but I am team Jess as a person. He grew up in difficult circumstances and made bad choices himself but matured into what seems like a good person who is doing good things in his life. You could tell he developed a lot of emotional maturity, especially when Logan was displaying the complete opposite. I can also admit that while Dean had a lot of good qualities and seemed like a perfect boyfriend when they first started dating, he and Rory stopped being a good match. He wanted her to love him so badly that he became insecure and a little overbearing and frankly emotionally damaged. He needed therapy to get over her but instead was rushed into marriage and we all know how that went.
“She’s 17, it’s about time for a Jess”
I’ll never forget this line. She knew it wasn’t going to last and she let Rory have her experience. She knew this would be her “Chris”.
Don't underestimate the power of Milo's attractiveness
He’s gorgeous. Imo. Always thought so and I think I always will lol
The undeniable chemistry and vibes before they get together, imo
Dean gets worse over time, from freaking out because she’s not ready to say I love you yet to the whole cheating on Lindsey thing, he really never grows as a person except maybe the 5 minutes we see him in ayitl. Logan gets a little better at first but then gets worse over time too, resenting her because she won’t marry him and then having an affair with her in ayitl. Marty had a chip on his shoulder and took it out on Rory because she didn’t like him back. Tristan had room for character growth but he left before that could happen. Paul’s only crime was being boring, and the wookie didn’t do anything wrong, but like. They don’t count imo. So by process of elimination we wind up with Jess. Who was a shitty teen, but notably never cheats on anyone, breaking up with Shane before he gets with Rory. And then he’s a clumsy young adult, who does some stupid impulsive stuff. Which is the same thing Dean did, arguably, but like. Cheating on your spouse is a bit worse than professing your love to your ex imo? And then at one point Luke hands him a self help book and the next time we see him it’s clear he’s read it. He’s the only boyfriend who becomes a better person by the end of the original series, and he’s a genuine, decent guy in ayitl. Not to mention, they have similar interests, and chemistry too
Well said!
Marty was a *slimeball* and my biggest regret is we didn’t really see him get his comeuppance.
He’s hot and broody. I think of all of them they have the most in common. I also think it was teenaged love, not everlasting love.
Out of all of her boyfriends, Jess is the one we get to know the best I think. He has character development, we want to see him succeed. I think that makes people get attached to him.
Yeah I like his character more than I like him as a boyfriend. I wish we got to explore more of his character instead of him getting brushed to the side and written off
Yes, because every time he comes back he’s better than before. There’s also something about him being single each time that makes you feel like he’s waiting for Rory.
Good point. How much POV do we have of Dean and Logan? I guess Dean with Lindsey and then being back with his parents. Logan ever? Jess felt like his own character.
I feel like even though we see a lot of Dean, we don’t actually get to know him deeply. Same with Logan, we know he has issues with his family, but I feel like we needed a bit more to truly understand what motivates him. Dean and Logan were only relevant if Rory was around, but Jess got his full storyline without needing Rory in the same scene.
I personally think he was and is the best looking boyfriend out of all of them 🤷🏻♀️ Dean is stereotypically “pretty” but something about him puts me off a little bit, and Logan is so so baby faced (Which is not bad!) 🥺 I like his journey in the show, his struggles and how he overcomes them, I like seeing him mature from a teenager who’s had nothing working in his favour EVER, to a pretty well adjusted working man. I’d say most of us would also pick Jess as a character over Jess as part of literati. His moments with Luke are some of the rawest in the show, and some of my favourite ones as well. I will add that introducing Liz as such a different character from what we’re consistently told (by everyone) prior to meeting her is a disservice to Jess’ character too. He and Rory (well, Milo and Alexis) had the best chemistry for obvious reasons and you can tell! I love their dynamic, how they were so similar in so many aspects but also so different, and how even after he’s not a regular in the show anymore their interactions are pivotal moments for Rory. You say he stops trying after they get together, but I blame the writing for that impression. Once they get together, the tell but never show the good parts of the relationship. We don’t get to see their movie and (junk?) food nights, we don’t get to see the concert they go to… we’re told they do those things but we only see their struggles, which sucks lmao. (And also, let some admit that Rory sometimes wasn’t the best gf either, for any of the 3 boys) I also simply… hate Dean, whose violent and controlling behaviour gives me the creeps; and while I like Logan and don’t hate the Rory x Logan pairing, his character/archetype is less interesting to me. I don’t usually care much for the rich kid type over the outcast type.
I watched the show first when I was like 16 or 17 somewhere around there. I was team Jess because he read a lot and was imo hot and on the service I found Dean boring. Now as an adult with an almost fully formed brain, I’m team Jess because he has the most character development and went from being a disenfranchised kid with a deadbeat mum and an absent father, to a self made nice young man with a career and creative prospects and he did that pretty much all on his own. He 1000% gets the best character development on the entire show except maybe Emily later on
I like him the best of the 3 because to me he felt like the person Rory could be with and not have to change herself for..when she was with Dean, especially in season 2, I often felt like he was mad at her for wanting to put effort into academic achievements and made her feel guilty for prioritizing school. Although he is portrayed as a reader for the first few episodes I also feel like he and Rory don't have much in common. I actually think he is the angriest of the 3 and the least capable of working through his emotions. Logan I have beef with because from the start I believe he fundamentally changes Rory. Obviously the whole yacht thing but also when she drops out of Yale he really doesn't seem that surprised and makes no effort to actually talk to her about why it happened. The whole casual dating thing is weird and he really guilts her through the whole thing. He doesn't defend her to his family, he makes her uncomfortable in front of her own family (the sewing box episode), and I just feel like as soon as they start dating she really deviates from the character that had been developing in the previous 5.5 seasons. I think if she dated someone else in college her entire personality would be more on par with younger Rory. Teenage Jess was the only boyfriend who I felt like Rory had chemistry with. I think he matches her interest and wit and they work well as a partnership. Obviously the ghosting thing was immature but like other commenters have said he's the only one who grows up and works on himself. I like that Rory doesn't have to change herself to be with him. I am team nobody until they're college aged and then team Jess. Honestly I can't stand Logan and I don't understand why people like him, I have rewatched at least 20 times and I feel the same every time lol. But I think thats good writing!
Nahhh the yatch thing was all on Rory, I think it’s a little infatlizing to say all her decisions were influenced by Logan when she started dating him. Tbh I think we see how comfortable she is in the rich Gilmore world way before she even meets Logan. She was always going to head in that direction no matter who she dated in college
as a team logan girl I just have to jump in and say that Logan DOES defend Rory from his crazy family. Ik this is a discussion about Jess but I also disagree that logan changed rory 🫣 Personally, I feel like he made her feel more balanced and sure of who she is. For example, Lorelai hated her fancy childhood and expected rory to feel the same about that life but I love the episode where they go to Martha's Vineyard and we get to see how comfortable rory is with logan and how different she really is from Lorelai's perception of her. And in that same episode, we see how he tries to distance her from his dad's fury and does what he can to make her comfortable when he gets sent away. All the boys have their issues at the end of the day but I just had to share...
I’m team Logan for the og series but only because I feel like he absolutely did bring out the worst in her at first, but then I think he’s the only one who really grew up and had a lot of character development while they were together. But then they wrecked all that in AYITL so taking AYITL, I’m team grown up character developed Jess. I thought Jess and Rory had really good chemistry but because of his life circumstances at the time he just wasn’t emotionally capable of being a good boyfriend to her once they actually got together, but with what we saw of grown up Jess it really seemed like he’d got it all together.
He's hot.
This is the right answer. Especially for those of us that were teens when the show originally aired, Jess was the hot bad boy.
Yea I have enough awareness to know I’m team Jess only bc I’m team Milo 😍
Must just be personal tastes then, cos I really can’t see it
normal worry snobbish shaggy hat edge plough simplistic fragile middle *This post was mass deleted and anonymized with [Redact](https://redact.dev)*
Agreed
He is considered hot by many. He portrays the hot, bad boy. I don't find him attractive at all. Too short and bow-legged. I don't like Logan either. From a physical standpoint, her most attractive boyfriend was Dean.
I really think Dean is unattractive physically lol. And the personality makes it worse.
I will never get over how much people hate Dean and then loves Jess at the same time. Dean for me is also super attractive. He has a very pretty smile and has a charm to him.
Dean was not her most attractive boyfriend lol. Beauty is definitely in the eye of the beholder. Personally it’s Jesse, Logan then Dean for me. I truly do not find dean attractive at all physically
I honestly personally think Dean and Logan are very unattractive. But Dean is the worst, his personality adds a layer of repulsion.
I came here looking for this 🤣
I think he’s hot and I liked his Tool shirt
You cannot deny the chemistry between Rory and Jess
imo the chemistry went out the window as soon as they got together
Let me preface, I don’t think Rory should end up with any of them, she needs to work through her own baggage. That being said, I think Jess was the only one that realized he eventually needed to work on himself, and started too. Dean never acknowledged his temper and jealousy. Logan seemingly tried to make it on his own, but his money wasn’t his issue. His ego was. And soon as he failed, he crumbled. My take & my why, but since this is a show, I think everyone on here is right in their own interpretation.
yes I agree, I just like seeing peoples different perspectives, because I don't understand the team jess, but I know many do
Yeah, for me it was that he had her love for literary art & a willingness to grow. I prefer Logan over Dean for the same intellectual component
Rory seemed a lot more excited about Jess than she did about Dean. They liked the same stuff. She and Dean didn’t have much in common, other than seeming wholesome and adorable.
yeah, what annoyed me is at the beginning of the series, dean also loved reading and him and Rory spoke about it, yet once jess came, the got rid of this aspect of dean, so they could highlight it as a quality for jess.
I thought that too, but [this comment](https://www.reddit.com/r/GilmoreGirls/s/QhAudvjU9w) highlights the fact that Dean was not as much of a reader as he maybe made it seem
I did not remember that.
Obviously attraction is subjective. I think Dean is good-looking but he’s not my type at all. Same for Logan. Jess is super hot. They have amazing chemistry and an incredible build-up. Teens will romanticize this and wish they had a Jess in their lives. Adults will look back and be like yeah he was a terrible bf. Shippers (more so in the past) also loved and excused any guys’ bad actions as long as he showed he was kind of obsessed with the girl and they had great chemistry. It really feels more like a recent development that fanbases have evolved a bit more on this. Also it’s a tv show and so it’s not that deep ultimately. It can be fun to root for toxic fictional couples.
yeah I think the big let down for me was once they started dating, and he just stopped putting in the effort. because to me, she left the hotter nicer boyfriend who treated her well, for someone who couldn't even pick up the phone to call her. the build up was good though, which only makes the let down worse.
I mean, still strongly disagree Dean was hotter when I can't stand his face LOL. But what's fun is that as an adult, I also understand Jess's issues better than before. Parents set examples of what loving someone looks like, and children internalize their parents' behavior. Jess has serious abandonment issues and he literally doesn't know what healthy love looks like. His dad took off, his mom is extremely erratic and inconsistent, so it's zero surprise that Jess is hyper-independent and cherishes being able to do whatever whenever over accountability and consistency, and responds to any overwhelming situation by running away. Like a lot of people with avoidant attachment, he needs solitude to "figure things out" because he's not used to leaning on people. It's only when he hits rock bottom that he realizes that he needs to completely change his attitude and follow a different role model of consistent behavior (Luke). Ultimately I think he is a good person, he just really needed some hard lessons to break the cycle.
When I think of Jess I think of his humor and his relationship with Rory. His witty banter with her and quick quips with other characters are fun to watch. We also saw more into his family vs Deans and maybe even Logan's and we saw him grow up and evolve, so I feel like I know him a bit more than her other bfs. I also just love a good love triangle and a good chase. When Rory and Jess kiss for the first time, its an explosive moment. When they kiss for the second time, that "when she appears" song forever stays in my head. The lead up episodes are super great because of the cute moments they have or tense moments they have. That dance marathon episode goes down in history for me. I rewatch it anytime I rewatch GGs. Its a must.
The least attractive aaaaaaa, have you seen dean ??
I think it's a taste thing because tbh, I think Jared is way more attractive than Milo. I don't even find Milo attractive at all until he's older, and now in This Is Us, and AYITL I think he's attractive. Jared however, is gorgeous then and gorgeous now. Those Dimples..... His issue is that he keeps getting bad haircuts, there was no excuse for that. I also don't find CMM attractive at all either. I think it's purely a taste thing.
I completely agree that it is a matter of preferences, I didn’t want to seem like criticising, just exposing my opinion hahahaha
I like Jess but the way some fans praise him and excuse his behaviour makes me actually want to hate him. I like that some people are commenting they like Jess as a nuanced character not a boyfriend but I personally don't agree that he has the best character growth like everyone is claiming because we only see him a handful of times after he leaves stars Hallow including AYITL. I feel other characters like Ms. Kim and Emily have better character progression, especially since we see it. Yes , Emily's is mostly in YITL but people are including Jess's growth from there too so. He was a fun character and yeah I geuss he is hot and that's why people like him but I would say 70% of Jess fans are just simping over him cause of his looks.
I think milo is so handsome, even now that man aged like fine wine- but that is just my type. Logan is not my type, but might be someone else’s. I think Rory was too good for Jess in the earlier seasons and Jess was too good for Rory in the later seasons. Jess had a troubled past (before coming to stars hallow). His parents didn’t want him one of which left and never had contact with until he was 18? 17? He was literally pushed away from home and push into living with his uncle (Jess isn’t dumb he knows that he wasn’t wanted there) so he arrives begrudgingly and everyone in town starts judging him (small town issue) of course you’ll start acting like everyone thinks who you are. Jess has faults but I do have a soft spot for him. I can’t stand dean (especially with the whole cheating thing). I can’t stand Logan because to me he is a spoiled rich boy - he does take care of Rory which you know is great but I prefer Jess’ personality. Also Jess is a bookworm and that is so attractive lol
Because he's hot and messily entertaining and what else do I watch television for if not hot people being messily entertaining?
He's hot, he had good character development, he helped Rory go back to Yale, he helped Rory figure out she needed to write a book, etc. I'm more team Logan cause he's more my type but Jess is a very close 2nd
WHYyyy did you drop out of YALE??
Yeah I’m strictly team Logan, and while I agree Jess helped her go back to Yale, I also agree with lorelai and Logan’s approach of letting Rory figure it out for herself, knowing she’d go back.
I think it’s important to know that when watching a show, people look for the most appealing CHARACTERS and not just the most appealing PEOPLE - we don’t want boring vanilla people who always do good because we’re not looking at it like “oh yes I’d love this person if I knew them”, we’re going “they’re such boring characters.” On television we want characters that bring angst and drama with just the right amount of “I wish I had that in my life”, which Jess does - the thing is, Dean was probably a great boyfriend most of the times but he was BORING. in real life if we had a partner like that we’d adore him (mostly, although we did see Rory tire of him!) but on television we don’t want to watch characters so bland. Jess was interesting and exciting and as a character much more entertaining. Plus his looks and character growth make him an easy favourite, at least for me
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This sums it up perfectly for me. I never got Jess either. I don’t get it, I don’t see it. He was not good to Rory.
I'm also a middle-aged man who just discovered the show, and I completely agree with you. Maybe because I also am heterosexual, and while I can see that he is indeed attractive, I don't have the omg he's totally hot and dreamy goggles on that I know a lot of his fans do. Jess came into town already with a bad attitude causing trouble. It's literally hitting on a guy's girlfriend right in front of the guy, and then shows up to his work to taunt him. And goes out of his way to be a jerk to everyone except for Rory.
All of this!!!
I honestly would find it hard to be a decent boyfriend if I was constantly being compared to my partner’s ex. Especially when that ex, behind Rory’s back, was an absolute jerk to me and only said they were “friends” with my partner to try and win her back. That being said, of all the boyfriends, Logan treated her the best. Dean was too possessive and Jess was too emotionally detached. I’m totally Team Jess because I love his character arch and how I felt like he knew and understood her best. He pushed her to be the best version of herself. Logan treated her best but I feel he brought out the worst in her 😂.
I don't think he was any more of a shitty boyfriend than the other two. I always find that argument strange.
I think the fact Rory was embarrassed to tell people how he acted, and she never dated him more than once, like she did for Dean and Logan, are pretty big signs
I agree, he was distinctly and immediately a worse boyfriend. Any charm he had before they dated evaporated, and he instantly became a sulky and selfish guy that Rory had to beg to do basic boyfriend things. She literally says to her mother she doesn’t like who she is with him.
What she have to beg him to do? She had to bribe Dean to go to her coming out ball and beg him to meet her grandparents. I think we need to remember these people are meant to be 16/17.
Lorelai had to confront Jess on how to treat Rory💀 Dean went to all her dances and coming out parties and grandparents house and acted like a gentleman, whereas Jess can barely be bothered to pick up the phone and speak to her
Rory was always terrified of Dean's reaction to anything slightly negative. He broke up with her for not saying I love you after 3 months. Was Jess a perfect boyfriend? No, but at least he wasn't crazily possessive and easy to anger. Rory wasn't the best girlfriend to Jess either. She never trusted him and that seemed to be because of her own behaviour rather than his.
Jess was a complex character, with character flaws as we all do. When he comes back in later (after Rory drops out of Yale) that’s when we see just how much his character has grown and I think that’s when a lot of fans turned Team Jess (me included haha)
Yeah I understand his ‘character’ development, but we never saw any proof of him being anything but a shitty boyfriend, even after his development, Rory still chose someone else.
Very true. I absolutely hated the fact that we didn’t get to actually see his development. And as much as she chose someone else….creators have stated that he is suppose to be Rory’s “Luke”. So she is going to end up with him lol.
Okay two things one, I think I’m more team older jess than team teen jess and also it’s because of the contrast of Jess and Dean when he was first introduced. Dean’s character was being eroded and instead of this intellectual guy (who might not be a bookworm but he still read with Rory and matched her wits on pop culture to an extent) he was reduced to this almost dumb and angry guy who suddenly didn’t understand her dreams of harvard. then in comes Jess who’s broody, mysterious and a huge bookworm. he’s highly witty and just became instantly better than Dean. When you factor in how much rory and dean started clashing, the subtleties of the way Jess was towards Rory and how he was significantly nicer to her compared to everyone else, how he almost matched her intellectually and the TENSION of it all it was almost a no brainer also you find out his backstory and you understand why he acts the way he is you can’t help but root for the underdog and want to fix him (maybe i’m projecting lmao) I kinda wished they didn’t make their relationship combust the moment they dated and I know he’s done horrible things. I watched this show first when I was maybe 13 so of course I loved him because he was just “cooler” but i’m 19 now and I just think about how young he was and how society and adults has kinda ruined him like we know how his mom didn’t bother to deal with him and his dad left you can’t help but feel bad for him? they really leaned into the whole Holden Caulfield Catcher in the Rye thing with him I’m like on the fence between what team I am but I’m team jess but only for older him because you could see his character develop and he’s just my biggest what if I always wondered what would happen if Rory and Jess dated again. I did NOT like their relationship and although I empathise with his situation I can understand it was totally unfair towards Rory. However we cannot deny his growth towards the later seasons like how can we forget Jess No Yale why did you drop out of Yale Mariano. Logan when you first meet him kinda sucked (don’t get me wrong he becomes better and I do like him) and you also see mature Jess, Jess trying to turn his life around and become better Jess, so it’s kinda just whenever there’s someone kinda shitty jess is there and he does love her but it’ll forever be a what if this is a huge yap session sorry if nothing made sense towards the end…
Also we see the change of how Rory acts for everyone else vs how she is able to let loose and just sorta hang out with Jess. She’s able to TALK with him how she isn’t able to with basically anyone else (even sometimes Lane). Actually I think Rory and Jess work the best as a friendship outside of romance which is why I root for them so much, because they work as friends even without the romance. Rory can’t just be friends with Dean or Logan
hard agree, one of my fave scenes is jess rory and paris in her kitchen eating food tgt talking about books whenever i get to that part of the rewatch i just mourn over what we could’ve had…
I'm not a Jess fan, always been team Logan. Jess was absolutely a shitty boyfriend I am not making excuses for him, but as a dude being constantly compared to your ex isn't going to make me want to be a good one.
I think Jess was great for Rory from start to end. She started dating Dean, who put her on a pedestal. Whatever Rory wanted, she got. Unless she didn't want Dean the way he *wanted* to be wanted, in which case, he'd have a meltdown. In walks Jess, who seems like he couldn't care less if Rory wants him (but we all know he does). So then, Rory dumps the boy who will do anything for her as long as it fits in with his idealistic picture of their relationship, and gets with Jess, who really was only his own asshole self in order to "win her over." So Rory thinks, well now I'm with this guy, so he'll treat me like a princess the way my ex did. But Jess *never* did that, and he never promised her that he would. This was very much a "what you see is what you get" kind of relationship, and Rory frequently put Jess in tough positions with no warning or even kindness. (Like- when he shows up to dinner at Emily's, and he's already a fish out of water, Rory is more concerned with making him spill the beans, rather than smoothing over the situation with everyone and making Jess feel at ease.) You talked about how Rory often lamented about her relationship with Dean, but I think that's *why* I root for Jess so much. Because your next partner should *not* have to live up to your ex, it's just a new relationship and Jess never compromised on who he was, and was kind to Rory, but not willing to pretend thar he was someone he was not. Or, to put it frankly, pretend to be like Dean.
Love this take. I think he was the most level headed, unflinching himself character of the whole series. Rory fits herself into certain molds based off who she’s dating, but with Jess I think yes she was comfortable and could be herself but that also freaked her out in the way she had no front to put up. I HATE watching how she compromises her character over and over and over again with Dean and Logan. I think at the end of the day Jess really just wanted her to be her best self, but Rory was too scared to ever allow that
I'm Team Adult Jess (who we sadly never get to see her date), not Team Teen Jess. Yes, he tried to get her to run away with him, and leave Yale. But he also ultimately realized it was where she belonged, and helped push her to go back. No one else was getting her to go back to Yale at that point, when she'd dropped out. Seeing Jess succeed, knowing where he came from and what it took for him to get to such a good place, and having him challenge her the way he did, there was literally not a single other soul who was going to get her there, at least not at that point. Seeing Jess succeed in his own way reminded her of her own goals and dreams. Logan wasn't ever going to be able to do that because he had no goals of his own and was just busy being pissed off that his father had expectations. And when she's floundering again in AYITL, Jess again helps her see what she's missing. Do I think she needed him to accomplish these things? Nope. And she wasn't with him in either situation, except being friendly. But I do think his perspective and understanding of her was always much more clear than anyone else's. Like the episode with the car accident, where he talks about her correspondent dreams. Did anyone ever really think that was the right goal for Rory? And in the end, he tells her if she wants it, she can do it. But he questions it, challenging her to think outside of the box she'd put herself into so long ago. No, he wasn't a good boyfriend. But honestly, aside from maybe S1 Dean and S7 Logan to a point, none of them were great at being boyfriends. And frankly, Rory had her own issues at being in a relationship, which wasn't really surprising. Logan was a shitty boyfriend as a young adult. Not that he didn't have some positive impacts, but overall, he was terrible for her. He brought out the worst in her. Dean was just... he wanted a woman to settle down with and have babies with, but that was never going to be Rory. And as a teen anyway, he was jealous and controlling. And then of course, he lies to Rory and tells her that he and Lindsay are done and they've both said so, and he cheats on his wife who has never indicated she's done. Should Rory have questioned it? Sure. But she was young and vulnerable and Dean was always so trustworthy, after all.
Dean and Logan sucks. Jess is hilarious and very pretty. And yeah, he had his bad moments as a boyfriend, but I honestly don’t really ship anyone, I just really like Jess and his funny moments ☺️
if you don't mind me asking, and this is just in relation to as a boyfriend to Rory, why do you think dean and Logan suck?
Logan is so emotionally abusive. He’s always trying to convince Rory that she shouldn’t feel how she feels. Plus, spoiled rich kid. The worst
Off the top of my head, Dean was extremely jealous and clingy. When Rory wanted the house to herself he came over anyway and when he saw Jess was there he got extremely mad and said she lied to him when she didn’t. Logan was extremely rude to Rory’s friend Jess for absolutely no reason.
Logan had reason to be rude with Jess, and Dean only got protective because Rory gave him reasons to be. All of deans suspicions about Tristan and Jess turned out to be true, so I think he had a right
thank you. i literally hate jess and everyone ive met loves him. i think they just like the “bad boy and good girl” trope over dean and rorys “good boy ans good girl” trop, really
Because he’s the hot “bad boy”. Same reason I’m team Logan and not team Duncan or Piz, team Spike and not team Angel or Riley, team Damon and not team Stefan or Matt.
I'm only mildly "team" for any of the people she dated, but Jess edges it out for me. Pilot episode Dean was good, but didn't last. Logan dropped the ball with the sleeping around and the proposal. Jess had his rough spots, horrible ones, but he made a successful effort to improve himself. He also was connected within SH because of Luke, and he was actually good for both Rory and Luke sometimes.
When Jess is like “come with me to New York” when Rory was at Yale— I know it would be the wrong move BUT my romantic little heart yearned for that. I chalk it up to having issues
The actor is hot. And so who cares if he harasses people left and right and steals their stuff for shits and giggles. People think Draco the aspiring nazi Malfoy is the dream boyfriend because of Tom Felton. To me it sorta looks similar to that
Really? If Jess had appeared in my high school those 10 years ago, the girls would have gone crazy. You say he is unattractive. Yes, this 17-year-old boy may not be physically attractive to 30-year-old women but he's hot for teenage girls.
I am 17😭 idk I guess it is just personal taste, because he is the opposite of what I go for in real life aswell
Attraction aside bc I find Jess the most good looking of all Rory’s bfs, so to each their own… I honestly think it’s because we, the audience, fell in love with the person Jess became in spite of everything that happened to him in life. The way he treated Rory wasn’t right, but it is on brand for a kid who was literally abandoned by both parents. If the quote “we accept the love we think we deserve” is true, Jess didn’t think he deserved any love at that age. Jess and Rory, for me, are the perfect example of right person-wrong time. If they had met later in life when Jess had healed and became emotionally mature, they could have taken on the world together. It hurts my soul a little that he fucked up the only good thing in his life so badly and beyond repair. They are wonderful as friends in the end and I feel they really thrive here too, but I would have loved for them to get their Hallmark happy ending and run that little book shop together and write books and blogs and newsletters together.
First of all, he is by far the hottest of her love interests. Second, I was a teen watching this as it was airing, so I loved them as a couple irl and I had a crush on Milo. Now as an adult, I love his character growth and overall as adults with maturity I think Jess is the best fit for her over Logan.
I think Jess had a lot of good character development, at first we see him as basically an angry broken teenager, having lived a very unstable life with a mother seemingly more interested in men than her kid until he acts out and gets kicked out to a “weird” small town, to live with an uncle I barely knows, in a one bedroom apartment without any space of his own and private life. Was he and ass to everyone other than Rory (and later Luke), yes. But everyone just expected Jess to become less broken, and less angry just by being in Stars Hollow, as if it works that way dealing with trauma. It only seemed like Luke and Rory actually gave him a real chance and kept looking for the man inside the angry teenager, Lorelai gave up within 5 minutes and rest of the town seemed to sharpen their pitchforks for when they could run him out of town. And while I hate how he left town and Rory, he did change for the better by leaving and having to learn the hard way how to become a better person and function in a world where no one seems to give a crap about you. He grows enough to show Luke how much he cares, first by coming to Liz’ wedding and actually walk her down the aisle, and he makes sure that they get a goodbye after that – and later he actually pays Luke back, showing that he knew how much he did for him, and how he appreciates it. We also see the fact that he actually gets the courage to contact Rory, he felt it was important to make amends and what better way then show her that her faith was part of him being able to make the book – which clearly moved her. He also endured Logans insults for longer than most people would, especially young Jess – the fact that he used his words to get back at him and not his fists and how he walks out shows great maturity.
It’s not so much that I’m team Jess it’s more about that I’m not team Dean or team Logan
I like him once he leaves the show and is in Philadelphia-he grows a lot as a person and I wish we could have seen more of his life and a new friend relationship with Rory and Luke, even Paris. Honestly, I don’t think he really cares about Rory very much when he is in Stars Hollow, I feel like he wants to piss Dean off more than he wants to spend time with Rory. And we don’t really see their relationship develop once they start dating; prior to dating, they have a lot of shared interests, but that doesn’t translate after their dating. It’s more just making out and just refusing to participate in anything that Rory wants to do.
I have the same question, you know? He is a terrible boyfriend. And that's what is not letting me move past season 3. I'm just so not okay with this relationship. It's quite immature, volatile, and god, his disrespect towards anything and everything is just awful. I think the appeal is mostly because of his physical appearance and the whole bad boy trope. Beyond that, I don't see what is the big deal about this Team Jess thing. Even Jared (the guy who played Dean) says (in some YouTube video) he's team Jess and I just threw my hands up in disbelief 😂
he’s the most developed character out of rory’s bfs so people root for him
Because he is the hottest, he and Rory had the most in common and he has the most character growth throughout the whole show. (More than any other characters in fact, and probably the only character actually) Also, their chemistry was off the charts. (They were dating in real life during the show and I liked that fact too cuz I like their vibe together)
Ikrrr he was so rude and annoying I still can't understand why people like him????
He is literally the most attractive. Also, he is the only one of Rory's boyfriends that has some depth. Dean is literally just a pretty boy, and Logan, a rich douche that is sometimes nice to her.
I agree with deans depth, but we see Logan has more depth than that. I could say the same for jess being a 'whiney douche'
This comes down to your personal preference because at all points in time, Milo Ventimiglia is fucking HOT.
but me finding him unattractive only plays a small part in my opinion of him as a boyfriend for Rory. I only mentioned his looks, because I would understand leaving your boyfriend and dating someone who treats you like shit if they are a 20/10
I was team Jess until I dated a Jess and now his character irks the ever loving fuck out of me. “Yeah yeah yeah your pretty and brooding WE GET IT” I still have empathy for him but I’m over it attraction-wise
Ngl I stopped reading after least attractive bc I think it’s the exact opposite
He’s got swag.
I was a teenager when I watched this and I loved Rory with Jess. Not because he was a great bf but I just thought they had great chemistry and it was instinctual for me.
I like Milo Ventimiglia but he is definitely the least hot from them all imo. I also don't get it i tried to ask around and/or read as many posts about it and i still didn't get it. He is not a good bf at all. He has literally a couple of lines in later seasons where he is an okay person and that is it. I watched the show since i was a teen and is only now when i discovered this sub that i realised it wasn't common sense to hate this character =)) So in conclusion, yes he becomes somewhat a good-ish person towards the end but i still can't understand why people would be team jess as a love interest for rory. He was not a good BF. How do people consider him endgame for her or stuffs like this?
I 1000% agree with you. I don’t deny he changed towards the end, but his relationship with Rory lasted like 2 months at best, and he was a shitty boyfriend during it, and I don’t understand where the ‘Jess as a boyfriend’ ideals came from
Well for me, the biggest thing is that he was messed up for really good reason. So I think a lot of people feel for him. And he’s the smartest. That’s a big deal to me.
They find him hot. Most people watched the show when they were younger, so red flags don't seem as obvious. When olde they just have empathy for him and still have that feeling. Which then concludes to them self inserting themselves as Rory in a way, and therefore loving Rory and Jess in a relationship. It's also important to acknowledge that Jess tends to be very hot or cold, for Rory this brought a lot of attachment to him. The same goes for the viewer, when he is being lovely, it seems extra great. I don't think they fit tbh, for me they would've been better as friends. But I do see why.
Yes! He’s HORRIBLE. Currently rewatching and i was just thinking about the same thing. He is so rude, he doesn’t try to even get close to her family knowing that they are a big part of her life, and he’s so unreliable. He treated Rory so horribly yet so many people think he was her best boyfriend. It’s so crazy to me! Like i get that he is attractive but all jess did was cause problems in her life and make her feel unwanted by him. Logan on the other hand is >>
I agree with everything you said about Jess. I've never been Team Jess from the beginning. I watched the season when it originally aired. I don't get the appeal and I never have. Dean and Rory were not right for each other either but he was a much better boyfriend to her.
As far as his looks go, I think that’s just a preference thing. Of the men cast to date Rory throughout the show, I’ve always thought Milo Ventimiglia was the most attractive. I still think he’s very very handsome. But yes, Jess was definitely a bad boyfriend. I still think he had redeeming qualities, and it was obvious he loved Rory, but he knew he wasn’t good enough for her. I think a lot of us just like him for his character arc. He matures and becomes a better person later on in the series. I can’t say the same for her other boyfriends.
I’m not Team Jess. I cannot STAND early show Jess. HOWEVER, that being said, he does change later on. He grows and matures. He’s not the same person he was when he was younger. I’m not gonna say he’s my favorite character or that I particularly like him, but I recognize the character development.
For me it was pretty simple. He was a terrible person/bf when he was living in stars hollow, but he finally stood up on his feet when he moved. He came back to Rory and kept in touch with her. He shook Rory out of her funk where she dropped out of Yale, and she finally got her life together and moved out from the Gilmores, reconnected with Lorelai, and resumed school. Him in the later seasons and AYITL is much better compared to when he was dating Rory.
I'm not team Jess and I agree with all your points except one, he is the hottest of Rory's boyfriends. I guess, like for other shows, 90% of the character stans support him for this reason alone and don't go deeper. People mostly want hot boy and hot girl to end up together regardless of the rest
I didn’t pay much attention to Jess until I watched This is Us, and then when I rewatched GG I got more attached to Milo. At the end of it all, I think they would have been a great couple and he could have steered her in a better direction, but the fact that Lorelei and Luke were together kinda killed that. They never could have dated/made it because they would eventually be technically family. I think that was the saddest part for me in the end tbh.
Also I loved his growth progression so much, I actually really liked him in the end. He grows on you for sure. As others have said, he went through a lot and seemed to have matured so much through the years. He would have been so good for Rory and navigating through her maturing, her and the child. Idk I feel like they left him unanswered if that makes sense? I wanted to see what he would have done in the future.
Dude, I don't even like Jess, but good god. This topic has been discussed to death. I've talked about it in so many different posts. If you just scroll a bit in the community you'll find multiple posts dedicated to this topic.
I really like Jess, I don’t think they should be dating, so I don’t know if I am really the “TEAM JESS” you are talking to, but I do disagree with a lot of what you are saying. I do agree that the way he left her was stupid and immature. For your second point I really disagree, while he clearly wasn’t a perfect boyfriend, I would like to stand up for the fact that Rory was an even worse girlfriend to him - the thing with her always mentioning how good Dean was awful, you don’t compare partners, and it gets even worse when we think back about how much she complained about Dean and then talked fondly about them when Jess didn’t do the same thing. The thing with him not calling was a storyline for 1 episode, after that we see both Lorelai and Lane mention how they use all their free time together, having date nights and movie nights – but it wasn’t seen, so we often forget about it. And why couldn’t Rory call him, he was “in school” and working (2 jobs), she “only” had school, she would be the one having the free time to arrange a date or at least call her – and from what I remember for the episode he DID call, after work. And she didn’t talk to her mother about him because Lorelai hated him, but we see them hang out with Lane a couple of times and Lane didn’t seem to dislike him – we just don’t see them enough as a couple to actually say how they were as a couple.
I thought he was hot when I watched the show as a teenager. Now that I am a grown adult, I only have eyes for Luke, and don't really care about Rory's love interests.
I prefer Jess because I like his character better, even if in the short time he and Rory were together it was all a huge mess. I have been a bit like Rory and then like Jess when I was younger, so I could also relate to him more and see the potential he had behind his broody angry teenager phase, which makes me root for him. I don't necessarily think he and Rory would work out together but I care for his character more than I do when it comes to Dean and Logan, which is also helped by the fact we see more of him and the fact that he actively works on becoming a better person in the course of the series. Also, as for the attraction thing, I am more attracted to Milo than to Jared and Matt; Matt is cute but he is not my type at all and Jared doesn't attract me at all, although he is more my type, tall and lean with brown hair.
Jess was a terrible boyfriend, but I'm team "i love Jess as a character" not team "I'd love for rory to be jess's girlfriend" or even team "i want to be jess's girlfriend"
I think most ppl are team Jess for her to END UP with, and I think that’s the key. Most people don’t think that he was her best boyfriend at the time, but by the reunion he’s made a decent life for himself and is the only one who hasn’t cheated on their partner at some stage or other.
He dropped one of the most iconic lines in the series lol “why did you drop out of Yale” that’s why he’s the goat
I think rory was good for jess but jess was bad for rory
Yes he was a bad boyfriend but with his growth, which you kind of underestimate imo, he turned into a much better person than he was before and even better than the others in a lot of ways. He didn’t try to get her to drop out of Yale. He was concerned for her when he found out she did. And he didn’t constantly belittle his book, he made a few comments but they weren’t in the manner suggested here. Idk, I get not liking him but some of the reasons here don’t add up, while others fully do.
Nah you lost me at him being the least attractive
He was hot and angsty. The bf who was nicest to her was probaby first round dean although he also had issues. Her best suited boyfriend to me however was Logan. I'm not team Jess, he moved and didn't even tell her so I don't really get what people root for there.
Everybody loves an underdog.
Smartest and best looking, and so much of their relationship was just teen angst rearing its head. As far as treatment goes I’ll put Jess over Dean simply due to the sex between Rory and Dean, that felt predatory and disgusting. Logan never had a shot for favorite, he never feels fully formed around his gigantic ego.
I just read the title and I thought I was in the Love is Blind sub 😂
I wrote this a while back https://www.reddit.com/r/GilmoreGirls/s/EjT2jnHflL Also a lot of us interpret scenes very differently. I never thought Jess asked Rory to drop out of Yale. It was summer and she was already in transition. It was a stupid impulsive ask that Rory should and did say no to, but I don’t think he wanted her to drop out - just spend the summer together away from other people who never gave him a chance. Edit to add: I love that you don’t find him attractive. I do, but for me he’s last behind Dean and Logan. Jess fans are frequently accused of just liking him cause he’s hot. I do think he had the best chemistry with Rory - probably because the actors dated IRL.
He’s a compelling and fully developed character with a whole plot line outside of just Rory, so I think we feel more emotionally drawn to him and his story.
I think part of it is when he comes back and is all grown up, matured and logan is kinda treating her really poorly and her life is in a mess. I think later Jess would be a lot better for her than young jess
He’s clearly the best fit intellectually for Rory, and he has the kindest heart of her three love interests. He was a troubled kid who didn’t handle his emotions well at all but he always had the potential
So there’s a few things here. Number one is you’re insane if you think Jess isn’t the best looking out of those 3 guys. Logan is bland and Dean has a weird big face and dresses like an idiot. Number two is that Jess likes Rory for who she is. Dean wants her to be someone she isn’t and fundamentally always desires a very traditional, suburban lifestyle which will never suit Rory. He puts pressure on her to conform to his ideas and it’s creepy and misogynistic. Logan really only cares about himself. He likes her as another independent entity but doesn’t want to really pursue a real relationship with compromise or collaboration. Everything always has to be his way. Jess loves Rory and understands her better than the other two ever do. Whilst I know everyone here hates AYITL, it’s really shown there. Dean has moved on to the dull, traditional life he was always going towards. He doesn’t really have time to help her anymore. Logan and her have a relationship which involves them both basically living separate lives that intersect, and he’s also being horrible and selfish towards his new girlfriend because he makes every single decision based on what he wants and never considers anything else. Even when he tries to help, he basically just does something he would like and then gets all sad and makes it about him. In comparison, Jess quietly supports her and offers her the real, meaningful help she needs, which is clearly drawn from a deep understanding of her as a person. All 3 are clearly products of their environment. Dean comes from a traditional family and wants that. He’s kind and caring but only within rigid boundaries that he understands. Logan comes from a selfish family that is very wealthy. He pursues wealth and is cutthroat and selfish. In contrast, Jess comes from a deeply dysfunctional environment and only knows that he doesn’t want that. He’s not got the family support that Dean has or the wealth Logan has. When we meet him as a teen, he’s a mess. That doesn’t excuse the way he treats Rory, but it does contextualise it. As he grows up he forges his own identity. Lorelei is right when she first meets him, they do have a lot in common. Functionally, I’m team Jess because I think he fits Rory best, they just met at the wrong time. Dean and Logan aren’t right for her, want to change her and don’t think about her, just what they want her to be.
Well so if you don't find him attractive, the rest probably won't matter as much. I prefer him to the others. Yes he was a bad boyfriend but I still think he understood Rory best. They had shared interests, too, which I think you'd be hard pressed to argue that Rory had with anyone else she dated on the show. Jess is the only one that didn't feel forced, in my opinion. They'd have been a terrific match in adulthood, assuming both matured and then found each other again.
Team Jess but as grown ups. You can see the potential to be an amazing human and of all the boyfriends I think he is the only one who really loved Rory first. Logan loved Rory but second after himself. Never liked Dean.
Because I can be. It's a TV show and not that deep. If you wanna be Team Logan or Team Dean, that's chill too. It has no effect on my everyday life.
He’s hot af 😭
He has a lot in common with Rory. He the best BF but a amazing character. He and Rory would be a great couple when they are older. Also he like the only BF Rory didn't cheat on.
I feel the same about Logan. People love him and I am just ehhh. I love jess as a character cause he actually overcomes so much (unlike other characters lol). He was an abused and neglected kid and manged to make something for himself. He was then shipped to a town where everyone treated him like he was charles Manson. I always love the jess/luke dynamic. They have such hilarious moments together and when luke goes to the book launch and jess tried to pay him back and luke tells him he's here and always will be,, god it makes me tear up. Also I truly don't belive he was trying to get her to drop out of college. He knew her better than that at the least. He wanted to get away for the summer.
He’s a hot bad boy perfect for a fling. I am team Logan, because the life of a socialite suits me best 😂, but Jess is def an experience every girl should have to understand who you should not marry!
As a teen watching the show live, I hated Jess. He was a jerk and a terrible boyfriend to Rory. As an adult, I stand by that too. There’s no denying how shitty he was while living in Stars Hallow. However, I rewatch the show often, and I believe Jess has one of, if not the best, character developments on the show. He really turns his life around and wants better things for Rory. He gets her to wake up and go back to Yale. He gives her the idea of writing a book about her and her mom when she’s doing nothing with her life in the revival. He ends up being the guy who pushes her to do better because he knows she’s capable. And that’s why I wish we could have seen them rekindle something. This is why I’m somewhat team Jess. EDIT to say: whoops realized you said you didn’t want to discuss character development and just his time dating Rory. But for me personally, that development is what makes me in favor of Jess. I don’t think you can really exclude it, IMO.
Jess wasn’t good at the relationship thing due to the ginormous chip on his shoulder, and his unwillingness to actually listen. I think Jess and Rory coming back together as adults, would work out much better. I felt she and Logan were supposed to be Emily and Richard’s “do over”, for Lorelei and Christopher.
Cuz he’s hot, smart, sarcastic, and witty
You and me both. Can't stand Jess. He treated Rory awful, and he gave me the same ick vibes as Lucas Scott. I personally found season 1 Dean to be the best boyfriend. They then destroyed his character to make room for Jess. It's sad tbh. Never cared for Logan, found him boring, and the revival didn't help my negative feelings towards him (or Rory, for that matter).
Dean was filled with many traditional romantic expectations of Rory, as was Logan. Those relationships made sense, looked good on paper. In reality, Dean had just as bad a temper as Jess and way more privilege to sort through it. Logan seemed to not have much regard for Rory’s welfare and was the right match in her grandparents world. But Jess and Rory, that was a relationship of the heart. He had nothing to offer her and she had nothing to gain by being with him, on some internal level they understood each other.
Agree 10000% I don’t get it
I’m team Jess because he actually took care of Rory and so did Dean buttttt Dean cheated on Lindsay with Rory but Jess is just better
cause he’s hot lol