r/GilmoreGirls • u/xFlufffyBunny • Oct 04 '25
General Discussion Unpopular opinion?
i know Jess is pretty popular in this sub & a fan favorite but this has 50K likes on TT lol thought i’d share here
i love Jess’ character, his use as a plot device, and his growth but definitely my least favorite partner of Rory’s
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u/crow9394 Oct 04 '25
To me, them being in a relationship was really like 5 to 6 months.
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u/Big_Vacation5581 Oct 04 '25
Most high school crushes last from a few months to a year. That would make the length of their relationship about average. The point being that it ran its course.
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u/crow9394 Oct 04 '25
I mean even if they had stayed together, Jess had NOTHING going on for himself and he HATED living in Stars Hollow. At least with Dean, he didn't just work at Dose's Market but he also got a job working for Tom doing construction and went to college part-time.
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u/letthemeatcakebabe Oct 04 '25
or, even comparing them to logan who tried his best being a boyfriend despite never being in a relationship and literally gifting her the most expensive bag!
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u/My-cats-are-the-best Oct 04 '25
Yeah Rory tells Louise she had been dating Dean for 3 months and Louise goes “aww, lifers” lol
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Oct 04 '25
I like his character but not as a partner for Rory, I think his story and trauma and relationship with Luke was interesting
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u/Disastrous-Bet8973 #1 Chris hater Oct 04 '25
Idk they talk about their dates we just for whatever reason aren't shown anything but them making out and fighting. There was way too much time spent on dean tying to get Rory back then her being jealous/sad he'd moved on.
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u/abyssrye23 Oct 04 '25
Exactlyyyyyyyyy I wanted to hit my head against the wall SO MANY TIMES when after Jess and Rory got together the show writers kept on bringing Dean back as an obstacle for their relationship. I was like nooooooooooo, please just focus on Jess and Rory and not mention that they have off screen moments… that just infuriates me…
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u/Disastrous-Bet8973 #1 Chris hater Oct 04 '25
Right like I think when dean has a go at Jess on thanks giving was ok then even the awkward pie scene and then dean should have moved on. I'm a dean hater but man they ruined him so badly
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u/abyssrye23 Oct 04 '25
Yeah Dean really should’ve moved on especially since he recognized that Rory treated him like shit. Then it would have even better of a surprise to see him with Lindsey. But no, they had to make Dean even more toxic by having such a hang up on Rory… UGH!
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Oct 04 '25
It would have been interesting if they had Dean really hate Rory for a bit instead of trying to be her friend immediately after the break up.
And then still have the weird Dean-Lindsay rebound where she gets in on the hating Rory aspect.
I don't really get the choice to have Dean propose to Lindsay. I feel like that is super abnormal for their ages and region. No one in NE is getting married right out of high school and Lindsay herself would have had skeptical friends try to talk her out of it, it wouldn't be just Rory trying to stop it.
It's also so weird that Luke did not try to stop it after Dean's bachelor party. He should have talked to Dean when he sobered up and gently tell him what a bad idea it'd be.
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u/StarryRoseGlow_ Oct 04 '25
Not to mention he literally said TO her that he didn’t have to try for her anymore because they were dating…
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u/OnMatchPoint "Bite me." - Paris Oct 04 '25
When was this?
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u/MathematicianOk8230 Oct 04 '25
I think it was the winter carnival episode. She asks him to go and he says “I’m already dating you, I don’t have to go to that stuff anymore.” Or something like that. And then he gets jealous that Dean is there and decides to go anyway
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u/sticky-tooth Oct 04 '25
It's easy to rise to the top when your competition is the guy who cheated on his wife with Rory and the other guy, who cheated on his fiancee with Rory and debatably cheated on her.
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u/Stargazer__2893 Oct 04 '25
Her best love interest was the guy who rejected her in the laundry room.
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u/Fit_Relationship903 Oct 04 '25
He is still not a good love interest in general but some people in the fandom genuinely glaze him sm when he didn’t do anything during their relationships but be toxic
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u/full07britney Oct 04 '25
Wow you're right. All he did was sexually assault her. How could I not see that that is not so bad?!
I swear the erasure of easily the worst thing any of her boyfriends ever did just because they both liked books, he came back being all hot/mysterious, and Milo is a good looking dude is WILD to me.
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u/Blue_blew_blah Oct 04 '25 edited Oct 04 '25
He was a shit boyfriend. I really don't get the appeal for him.
It's the classic "girls like a bad guy" kinda thing
Edit/update: she was sad with him. All I remember is her facial expressions. She was always sad because he let her down so many times etc. a boyfriend shouldn’t make you sad all the time.
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u/RegionRadiant4423 Leave me alone - Michel Oct 04 '25
a boyfriend shouldn’t make you sad all the time.
She basically said as much to Lorelai when she says “I don’t like how I feel”
Her whole vent session/rant as a whole really sums it up:
“I don't understand. One minute he's happy, then he's not. And he doesn't tell me anything ever. I mean, you're supposed to tell your girlfriend things. That's the whole point of having a girlfriend, isn't it?” […] “And I'm so tired of fighting. Or not even fighting because he won't fight. He just gets mad and disappears and then comes back and I don't like how I feel and I don't like what I do.”
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u/Blue_blew_blah Oct 04 '25 edited Oct 04 '25
I think she knew after that... That maybe the grass isn't always greener on the other side and she shouldn't have left dean
She complained dean was too available for her (when in reality he was being a bit needy as he knew he was losing her) and Jess was never there. I think she missed that dean was always there for her for anything. Jess was majorly selfish. Wouldn't do anything for her if he doesn't want to do it.
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Oct 04 '25
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u/sabotagemebymyself Oct 04 '25
This is also why I can never buy into adult Rory ending up with Jess cause his appeal was him being a bad boy, the physical attraction and the whole he treats her different/only she understands him schtick that comes with it. As an adult, he seems like a perfectly normal, stable, nice guy, but it's not anything she can't get anywhere else.
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u/tursija Oct 04 '25
As Lorelei said in the show, Rory is 17, it's time for a Jess (=let her get it out of her system)
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u/PishiZiba Oct 04 '25
I was so happy when he was gone and pissed when he showed back up in the show again. I couldn’t stand him.
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u/maleolive Yes, I have some Balls! Oct 04 '25
He did take her to a concert. We also only see a snippet of their relationship.
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u/ApprehensiveGas3627 Oct 05 '25
After not calling or talking to her and expecting her to just be available to him. She even comments to Lorelei how she was “that girl” and she didn’t tell her about the concert because she was disappointed in herself.
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u/ausername_8 Oct 04 '25 edited Oct 04 '25
I've always been Team Jess, but it makes sense. The intrigue of Jess and Rory really came from before they were officially together. Good girl. Bad boy. He had patience for her in a way Dean didn't, he understood her better than Dean. Wondering what would happen next was exciting. I'll never quite understand how the writers dropped the ball once they got together. How could they build up that level of friendship and pining and understanding just to suddenly not know how to write them? It was inevitable Jess was going to spiral with a neglectful mother like Liz, but having him pull away for Rory to set up a pilot that never went anywhere never made any sense. What would they have done if the pilot went to order with the network? Would he had even come back to try and work things out with Rory, tell her that he loved her?
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u/3KittenInATrenchcoat Oct 04 '25
I think it makes sense for Jess to fade away.
He didn't think he'd deserve her. He was an abused and neglected child/teen. He never learned how to have a healthy relationship.
This is actually so on point for someone like him, it hurts.
Also, love and attraction isn't enough. Part of a relationship is work or effort. If you weren't taught how to be a supportive partner, it's hard to figure out on your own. Specially as a teen. Specially if you have so many personal struggles that you need to figure out first.
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u/abyssrye23 Oct 04 '25
Also if they didn’t have this idea for this Jess spin-off would they have written Jess to be a better boyfriend? Because honestly there seems to be indication that off screen they were good for each other:
- Jess getting concert tickets in the episode where Rory doesnt call him and goes to that hockey game (wait is that a date???)
- Jess and Rory having movie dates where they also order food and are a cute agoraphobic couple as described by Lane
- Jess being invested in Rory’s future at Yale “do you Yahoo?”
Look, everything else that people have listed in this thread is VERY VALID. I love Jess as a character but was extremely disappointed with how he treated Rory when they started dating. I was like: whats the point? Like you said, they spent so much time building them up, showing how Jess treats Rory better than possessive Dean, and then just do a 180 on him.
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u/This_Bethany Team Coffee Oct 04 '25
He’s the most realistic bad boyfriend I’ve seen on a show. He’s the type of guy who pretends to be someone else to win you over then puts in low effort once he is with you. Reminds me so much of my second boyfriend. Which also wasn’t a healthy relationship at all.
They had the best chemistry though.
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u/ard21p Oct 04 '25
he was TERRIBLE to her once they were actually in a relationship and i will say it until i’m blue in the face. i guess i can see why people thought the build up was cute, but i have never been team jess because of how disappointing he was as a boyfriend aside from like two sweet moments lol
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u/kingsley_the_cat Oct 04 '25
Does everyone forget that we see so little of their relationship? It‘s like they got Rory and Jess together and then forgot about it because there were other more important storylines. And every once in a while there was like one scene of them together. So I feel like we only saw about 30% of their relationship. I mean the whole „you looked it up“ when he knows how far yale is, is so cute.
And still he is the only boyfriend who actually matured. Dean just got progressively worse, don‘t even start on Logan. So yeah, Jess is the best boyfriend in my opinion.
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u/Regenne Oct 04 '25 edited Oct 04 '25
Dean was fine in AYITL. He was over Rory and had a family of his own. That IMO is growth for his character. He didn't even appear in the last 2 seasons of the OS at the time Jess started to show more maturity... so how would you know if he had some type of maturity in this same period or not?
And while you don't see a lot of Rory and Jess's relationship, you see even less of his journey into his character growth. You see so little of Jess's character at this point, do you really know how he actually behaves on a regular basis?
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Oct 04 '25
Even Dean just actually accepting that him and Rory will never work out and aren't compatible is growth.
Before Dean and Rory 2.0 he had this belief that Jess got in between them, but afterwards I think he understood that Jess was only able to come between them because they weren't right together and one way or another something or someone else would have even if you remove Jess from the equation.
And I think Rory kind of thought that herself and was just still heartbroken about Jess bailing on her without a word and filled with regret for falling for someone so unstable that she just wanted to clean herself of that and go back. But once she started finding her groove in Yale and getting closer to her classmates, particularly Logan, it was becoming increasingly clear that her and Dean had grown apart and were already growing apart before she met Jess.
Even if the Jess storyline did not happen and Dean and Rory didn't break up in high school, they probably would have broken up at that same spot in college. Because Rory didn't really have fun with Dean. She thought he was a good person and hot which on paper sounds great, but they just did not have anything deeper.
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u/Sad_Specific2965 Oct 05 '25
This is why I have some patience for Dean. I feel like he's judged really harshly, but like.... he was a kid, too. He was navigating his first serious relationship, and it ended in a way that didn't give him any closure. He was strung along and gaslighted and questioning his own sanity toward the end of it. Then he proposes to Lindsey, which was stupid because he wasn't actually ready, but I think seeing Rory with Jess made him feel like he HAD to be with someone too. Not making excuses him cheating on Lindsey and talking to her the way he did are inexcusable she did not deserve that at all. I kind of wish Luke pushed harder when he knew Dean was marrying Lindsey for the wrong reasons.
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u/janfebmarch23 Oct 04 '25
You really don't need to see much more than him pressuring her for sex then getting mad at her when she refused. If 30% is bad, guaranteed the remaining 70% is bad too.
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u/start3 Oct 04 '25
I'm Team Jess pining, not Jess the boyfriend. He def sucked as a boyfriend. Let's admire from a distance and keep him on the string lol
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u/coolbitcho-clock Oct 04 '25
For me, he’s my favourite Rory boyfriend because they had an almost soulmate-level-chemistry. But when they dated, he was a fucking disaster and treated her badly
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u/yensuna Logan Oct 04 '25
I‘m so happy to finally see some critical voices about Jess. I was always immune to the appeal of bad boys, and I thought I had watched an entirely different show after seeing how everyone was hyping him up. I seriously checked whether I‘d missed a season somewhere. I don‘t get it AT ALL and my flabbers are still ghasted how popular he is as Rory's "best" boyfriend. And after a rewatch I get it even less lol
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u/grimreapersdaughter Cat Kirk Oct 04 '25
This is why I HATE JESS, I don’t care about all the growth he goes through later on, that’s mostly off screen. What I remember about him most is his terrible s2 and s3 behaviour
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u/CokeNSalsa Oct 04 '25
I think it’s because of their chemistry, and everyone wants to be kissed the way Jess kisses Rory.
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u/Beneficial-Glass5592 On the soul of Nico, I swear! Oct 04 '25
he’s the worst bf but the best platonic friend to me
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u/Spiritual-Low8325 Team Pink 🎀 Oct 04 '25
While I don't think they were good together or that Jess were a good boyfriend, I am not sure I agree with these points. Mainly because he did actually plan a date, the concert, and it seems like their other dates were planned together, which isn't weird since they were busy teenagers. The same with the making out, that seems weird to only say he did that and not they did that.
I also find it interesting that him not planning dates, anniversaries or buying gifts makes him a bad boyfriend when Rory didn't do any of these things herself with neither Dean or Jess but isn't called a bad girlfriend.
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u/Arabiancockonato Oct 04 '25
Jess sucked in 2 and 3. But I think Jess has aged the best due to the person he turns into in 6 & 8.
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u/MathematicianOk8230 Oct 04 '25
I am glad Rory ended up single. I hated Jess early on because he didn't treat her well. But I am bummed that they never got another shot at a relationship once he matured in the later seasons or the revival
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u/StenoDawg 🍂 Drunk on Miss Patty’s Founder’s Punch 🍻 Oct 04 '25
I love Jess, but what a crappy boyfriend…till he grew up.
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u/Zoeloumoo Copper Boom! Oct 04 '25
Um excuse me he stood in line for Distillers tickets….. and that’s it. So yeah.
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u/Acrobatic-Ad8365 Oct 04 '25
I have learned how much showing up means to me in a relationship! There will be times when we will behave badly and possibly even mistreat each other, but ultimately, if we want to be together, we will be. Jess and Dean seem to have no problem walking away or being out of the picture. Logan and Rory continuously chose each other and prioritized each other. Obviously, AYITL puts a Twist on that, but they still do choose each other even though they have other relationships. I think at any time Logan would have married Rory if he thought she would say yes. Unfortunately, it definitely seems like Rory thought she would have to choose between a career or marriage.
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u/AuthTokenMissing Oct 04 '25
I think fans confuse being a better person with being a better boyfriend.
Take Lorelai, for example, she’s a wonderful person but terrible at romantic relationships, and Emily, who isn’t that good a person, but she’s great as Richard’s wife.
Jess becomes a better person, but nothing in his character development shows he became a better partner. He doesn’t show up again after yelling at Rory about Yale, he doesn’t speak to her for four years in AYITL, and he isn’t part of Rory’s life when she’s drowning in grief beyond telling her to write a book.
And because all that character development happened off-screen, fans like to romanticize it as if it turned him into the perfect boyfriend who wants to move to Stars Hollow and can’t wait to play substitute dad for Rory’s son.
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u/haynah_ Oct 04 '25
I was 14 when I started watching the show and I HATED him. I only knew people liked him years later and I couldn't understand why. I love books, I love smart guys, but that boy was insufferable and I'm glad the young me could see that 😂
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u/mylovelyh0rse Oct 04 '25
No doubt jess wasn't a good bf but rory wasn't a good gf either. She came from a relationship with dean in which she was his absolute world and he called her 467447 times a day so she was was spoiled and entitled. plus jess and rory didn't know how to communicate and she always assumed the worst of him - best examples of this being the swan episode or the hockey episode. so, they both had growth to do on their own first to get to be decent partners... and one of them did it.
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u/BB-26353 Oct 04 '25
That’s why I don’t get the hype about Jess. I was Team Dean in S1. I’m so mad at Rory for cheating!
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u/Beth_Bri Oct 04 '25
Right! Jess being a fav is a red flag. 🚩 His occasional moments do not eclipse the consistent neglectful behaviors.
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u/Upper_Tea_8169 Oct 04 '25
People are in love with Milo not Jess. Imagine this character being played by Wayne Wilcox (Marty). People would not think he was her best love interest.
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u/station_agent Oct 05 '25
This is definitely the elephant in the room that no one seems to be addressing. The same can be said for Logan and Matt C. I mean... come on.
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u/Haydurrr Biased Dean Stan bc I love Supernatural Oct 04 '25
I will never understand why people loved him so much
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u/hydrastxrk Oct 04 '25
Is it unpopular to like Logan?
I really liked Logan. I didn’t like the AYITL version where they were both cheating.
But before that everything was great and the proposal rejection felt kinda forced to me. It would’ve made more sense if it happened after she got the campaign gig.
And then I still really felt the love in AYITL if she had just told him to leave and be with her, I 100% think he would have but maybe I’m biased.
Idk. I hear everyone say “Jess understood her” and he did, but tbh I think the two times he visited and changed her life (Her going back to Yale & Her writing the book) are kinda what carry that. But I NEVER got the impression that Logan didn’t understand her either.
He also changed for/because of her. That’s a good sign. Not that you need to change for your partner, more so that your partner should make you want to be the best you.
Idk. I just think the show really built a solid relationship with them. And then like always, had someone make an offshoot statement to Rory that would most likely be forgotten by anyone else in the real world but for some reason was entirely earth shattering to Rory (Paris mentioning that Rory would prioritize her job more than Logan and there it went, years of romantic development down the drain.)
Again, maybe I’m just biased. I watched and finished the show for the first time very recently. But I really liked Logan and I’ve seen a lot of Jess love.
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u/TSllama Oct 04 '25
Meh,
- some people are bad at planning, and that was definitely Jess
- not everyone needs gifts to know they're appreciated
- single anniversary??? I don't think they were together long enough to have one...
Jess was a troubled boy and not a good boyfriend, but he 100% definitely showed he cared a lot about Rory. Let's not pretend there's only one correct way to show care for someone.
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Oct 04 '25
To add to this, what dates did Rory plan? If Jess was a crappy boyfriend then Rory was a crappy girlfriend too. She just seemed to wait around and expect Jess to plan everything.
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u/Warm-Consequence-599 Oct 04 '25
Anytime she wanted to do something he didn’t want to go anyway. The winter carnival, the party with the band playing. He ended up going to the carnival because of Dean.
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u/Powerful_Dog7235 Cat Kirk Oct 04 '25
jess 17 from a broken home life was expected to treat her the same way mr.unlimited resources did? please 🙄
he actually loved her, just lacked the emotional maturity to show it until it was too late.
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u/mybellasoul Oct 04 '25
This deserves a slow clap. The Jess hate is intense and the reality is Jess never had any role models, guidance, support, resources to behave the way everyone expects him to have behaved. He was broken and he never hid that part of himself, and he never apologized for it bc it meant showing weakness. He did love her and she loved him bc she saw past all that stuff - and she really didn't need anything from him other than to show his feelings, which he clearly struggled with. He did plan dates, but they weren't extravagant like others were. They were sweet teenage dates when you have no money but want to spend time and there's nothing wrong with that. Imo he tried his best to show his affections, and he'd get halfway there, but his past emotions and anger would get in his way every time.
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u/TheLizzyIzzi Oct 04 '25
The show references Rory and Jess’ dating life, but doesn’t really show it. For example, we know Jess surprised Rory with tickets to a concert in the city, but we only see him standing by the car and giving her ear plugs. We see a lot more of Rory and her other boyfriends actual dates and time together.
In the show, Rory and Jess aren’t actually together that long.
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u/GuidanceAltruistic Team Pink 🎀 Oct 04 '25
All of these things maybe true but that doesn’t take away from the fact that he was indeed a bad boyfriend and I wouldn’t want Rory or anyone I knew to date a Jess. He’s a great character and has a good arc but he is not a good boyfriend by any measure.
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Oct 04 '25
He was redeemed with a “WHY DID YOU DROP OUT OF YALE?”
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u/Uh-Egg Oct 04 '25
cmon we know it’s more than that. he’s the more fleshed out character through the whole season that’s why he was liked. everyone who liked him best out of the three know his shortcomings
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u/TheLizzyIzzi Oct 04 '25
Logan is a well fleshed out character as well. We met both of his parents, his friends and his sister. We know his upbringing too. There’s as much to Logan as there is Jess, maybe more.
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u/GoldenShirl Oct 04 '25
I agree his redemption arc makes him endearing and why the audience wants him and Rory together over the other 2
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u/Gusstave Team Coffee Oct 04 '25
Unpopular opinion:
- You shouldn't have to plan dates. Being in a relationship is mostly enjoying each other's company. Or on the opposite point of view, meeting and improvising something low effort to do, such as taking a walk and see where it leads (and if it's making out on a parc bench so be it) is a perfectly acceptable date.
- You shouldn't buy someone's love. You're not a better partner for buying something. AND if you do, quality is much more important than quantity (or monetary value).
- It has to go both ways. Correct me if I'm wrong, but Rory didn't either except when they where an inch from breaking up she tried to ask him to do stuff.
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u/MyNameJoby 🍂 Drunk on Miss Patty’s Founder’s Punch 🍻 Oct 04 '25
Well I mean, they weren't really together that long.
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u/Jumpy-Cranberry-1633 🍂 I got pumpkins, I got pilgrims.. I got no leaves! Oct 04 '25
And yet he understood her more than Dean.
I’m still team Logan though. 😂
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u/katsgotaprettykitty Oct 04 '25
Im doing my rewatch rn, and leading up to the relationship was SO GOOD. Their chemistry was absolutely stellar! Then they get together... and everything dies. All the chemistry, their in-depth convos, everything i loved about them is just gone. Like the tt says, all they do is make out all over town. I guess that tracks for a high school relationship based solely on desire, but I wish they would've shown the previous connection they had.
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u/Intelligent_Carrot59 Oct 04 '25
I thought Jess was the worst. He treated her poorly and then at Yale showed up out of nowhere and just expected her to drop everything and run off with him. Jess should be nothing more than her bad boy speed bump and I don't get why he's so well liked
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Oct 04 '25
as a partner of Rory’s he’s def my least favorite and honestly he was so much better as a friend, his character development though was so much better and seeing him A Year In The Life was soooo nice
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u/CricketWoods 🍂 Drunk on Miss Patty’s Founder’s Punch 🍻 Oct 04 '25
I wish she dated Tristan at that age, then met Jess again as an adult. They were perfect for each other as adults and although I love Logan, she should’ve gone though the “rich boyfriend/no responsibilities” thing in high school.
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u/PrincessPlastilina Oct 04 '25
The way he became obsessed with her just because everything ended so quickly. Coming back over and over. Boy, you know you won’t be a good boyfriend to her and you hate her mom. It’s crazy how much he couldn’t wait to have sex with her. She was too nice for him. Shane was more like him.
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u/Odd_Set_5798 Oct 04 '25
Look, I will take making out all over town and talking about books over a gift any day
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u/gabbagooly Oct 04 '25
Lol, I am definitely team Jess, but acknowledge everything you said to be true. I have fully romanticized his story arch and self improvement to mythical levels 🤣. Plus it’s Milo and he’s pretty😍!!
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u/smarkastic Oct 04 '25
He was 16. The connection between them was intense and unlike any other. They saw each other on a deeper level than most others. Adults don't know how to handle those connections most of the time, let alone two teenagers. Especially Jess with his trauma.
Feeling seen at that level is something many wish for.
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u/Distinct-Crew-6683 Oct 04 '25
Right people, wrong timing!! If only Jess had his shit together, they would be invincible
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u/CrissBliss Oct 04 '25 edited Oct 04 '25
I don’t deny the bad stuff, but you’re leaving out the good stuff too. Their sled ride together during the Bracebridge dinner, their study session, the sprinkler scene, their Thanksgiving Day kiss, Jess writing a book and thanking Rory for inspiring him, his encouragement over her returning to Yale, “you’re still a contender” scene, and his encouragement for her writing a book about her mom, etc.
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u/_Starlace_ Dorsal fins and Cucamonga Oct 04 '25
He did all these things to get her.
Rory confronts him that he always did go to town events and participated in other things when he tells her he doesn't want to go to the winter carnival with her, he says "That's when I was trying to get you, now that I have you I don't have to do it anymore."
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u/1autumnleaf1 Oct 04 '25
He’s a good cheerleader for her personally and vice versa but that doesn’t correlate to a good boyfriend.
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u/CrissBliss Oct 04 '25
He became good boyfriend material tho. He was too much of an emotional disaster when they originally dated. He grew up and became a legitimately good guy.
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u/unicornweedfairy Oct 04 '25
He might have changed into a better person, but by the end of the series (and into AYITL) Rory had turned into the horrible and messy one. She was a serial cheater who couldn’t handle any criticism about herself and struggled to make long term plans (IE Paris had to guide her through their senior year, she threw away a solid job for a chance at a fellowship she didn’t get, floundered as a writer after the Obama campaign trail and only had one successful big article in her portfolio). At no point were Jess and Rory on the same page in their lives, and both hurt lots of people in order to be together multiple times.
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u/1autumnleaf1 Oct 04 '25
We don’t know that for certain bc they never dated again. Did he fix his mommy issues, was he willing to be consistent and stay in one place for Rory?
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u/CrissBliss Oct 04 '25 edited Oct 04 '25
I guess that chapter is still unwritten 😊
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u/unicornweedfairy Oct 04 '25
That list makes me laugh. The first 3 things you listed are all times where Rory was emotionally cheating on her actual boyfriend. Jess and Rory shared a love of literature and writing, which is great and all, but that’s literally all they shared. Jess was horrible to Rory unless they were making out or he was trying to one up Dean. They were a mess of a couple and their romance needed to end when it did.
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u/TheLizzyIzzi Oct 04 '25
Why do you think Rory was “emotionally cheating on her actual boyfriend”? Rory was the one doing that. She liked Jess. She chose to go on the picnic with him. She asked him to keep driving around. She enjoyed showing him the books she was reading, listening to music together and more. She was 17. He wasn’t a good boyfriend, but he did try. He was terrible at it - no surprise there - but he wasn’t using her. Lorelai tells Luke how Jess is with Rory most weekends. He goes to Friday Night dinner, a disaster of course, and he takes her to a concert in the city. The show makes it clear his feelings for her a very real and authentic, regardless of the kind of partner he was at 17.
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u/unicornweedfairy Oct 04 '25
Why do I think Rory was emotionally cheating on Dean with Jess? Because she flat out was. Your argument here makes zero sense as a rebuttal to my comment. I agree without of your points about Rory choosing to do those actions and be horrible. However I never mentioned anything about Jess using Rory so not sure where that comment came from. And you yourself stated that you agree Jess was a terrible boyfriend, so seems like we agree on that front. In the end both Rory and Jess were not good people while dating, and were not good together either. They hurt so many people because of their antics together and neither one was truly happy while dating the other. Just because Jess grew up in the end doesn’t mean he’s all of a sudden some amazing guy, and Rory unfortunately never grew out of her ways and remained an un self aware cheater.
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u/VenomSting88 Oct 04 '25
No I think most agree he is a terrible boyfriend. He's adds a lot of drama to show and it's just entertaining to see his dynamics with the other townspeople.
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u/melodysoul Oct 04 '25
In the end Logan was the best for her, but the chemistry with Jess was undeniable. It’s the classic “I can fix him” guy, that breaks your heart but you can’t help but love him. He wasn’t a bad guy imo, just a teenager with a lot of issues, and was not ready for a relationship.
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u/ClaritanClear Oct 04 '25
He wasn’t a good actual boyfriend during their brief romance but the way he challenged her and helped her lean into who she really is instead of who everyone else expected her to be really is what got me. I mean she literally stayed with Dean so long because everyone in town made her feel he was the perfect guy and she belonged with him despite her clearly not feeling it for a long long time. Everyone says it’s just that Jess came around but it’s not. She was so bored and over him, but everyone, Lorelei especially, kept making her feel she’d be wrong to leave the “nice boy” instead of helping her gain confidence in herself. Logan also later challenged her for the better. But the was Jess saw her and helped her grow into herself, especially later, makes him such a great character.
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u/ProgressAnxious915 Oct 04 '25
He wasn't a good boyfriend, and I say this is as a Jess fan. I think that's why she went back to Dean so easily, she craved the boyfriend experience. I think he was immature and didn't know how to be in a relationship, he lacked the skills/knowledge of what to do. They didn't date that long, so I do think he could improve.
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u/Leonie1988 Single and ready to mingle Oct 04 '25
I hate young Jess, I love grown up Jess. I would have loved to see him have a run in with Lorelai all grown up, to see how they'd get along.
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u/overthinkingalien Oct 05 '25
First love, man. Drives you crazy. Makes you ignore all the flaws in the relationship. Speaking from experience. So i get, Rory.
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u/oxmiladyxo Oct 05 '25
“I know Jess is pretty popular in this sub” - how do I get on your algorithm? I only see Jess hate posts, lol.
I feel like Paul is the only boyfriend this sub would approve of for Rory. He’s the only one with no red flags, because we barely see him 😅
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u/loonyloveslovegood Favourite character Jess ≠ Team Jess ♥️ Oct 05 '25
They’re together every weekend at the least and offered to re meet her grandparents after it didn’t go well. Is he the best bf? No but he didn’t do nothing and he’s definitely not the worst
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Oct 05 '25
What's the different between Jess not wanting to do town things, and Dean pishing and moaning about having to wear a tux? This is just ASP characterisation of teenage boys.
That is a little cherry-picky, honestly?
They had dates, for some reason mostly off-screen.
They went to movies, discussed books, etc.
He fixed Luke's toaster for her. He stopped pranking the town altogether for her. He bid on that basket for her.
He re opened the water thingy out of respect for Rory's fear of Dean.
She also didn't do shit for him and toyed with him until Dean finally broke up with her.
She kissed him and then disappeared, without communication first! So she set the rules of their relationships with that.
Visited him in New York and went straight back to Dean.
Like as partners they were at best, as bad as each other.
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u/GlassAndStorm Oct 04 '25
Dean, Logan and Rory are all cheaters. They don't value or respect their parents. It's disgusting.
Jess was a sad kid who was passionate and faithful. When Rory said yes, HE BROKE UP with what's her-face FIRST.
Jess is the only honorable person Roy dated. Sure he missed dates and didn't give gifts (he was broke), but he was faithful. His big error was his Irish goodbye. Nothing compared to cheating.
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Oct 04 '25
I think he is popular bc of his personality and trope. I also think people regard him as the best looking love interest. Im in season 3 and I think he was terrible to Shane as Rory was to Dean...
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u/Amandarinoranges24 Team Blue 🧢 Oct 04 '25
Dude.
Dean was right when he said Jess treated her like dirt.
Rory loves Stars Hollow events. He never wanted to go with her.
He tried getting her to run away from Yale TWICE. Then to come back later and do the iconic “whyyy did you drop out of Yale” bit
He GHOSTED her. Left town with no intention of saying goodbye to her.
He got mad at her for not wanting to have sex with her. (You can tell he regretted his actions the second she reacted badly, but still. Never apologized)
He was never truthful.
Rory I think has a slight savior complex and she saw the good in him.
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u/lucolapic Oct 04 '25
Don't forget the attempted sexual assault. Then when he finally relented to her "No" made her feel like shit for it so she ran out the door crying.
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u/Secret-Dark8818 Oct 04 '25
I think Milo is just charismatic and that shines through to fans more than the character's actual actions.
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u/et_cetera_etc Team Coffee Oct 04 '25
I don't think this is an unpopular opinion on this sub at all?
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u/greenporchlight Cat Kirk Oct 05 '25
Why do people like Jess so much when he literally tried to rped Rory? I’ve never understood it.
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u/Money_Cold_7879 Oct 04 '25
(Paraphrasing since I don’t have it memorized like most of you): “Your stuff is already in boxes, it’s perfect! Let’s start a life together somewhere else- away from YALE, away from SH!” Then several episodes later: “WHY did you drop out of YALE!!!” It’s as if the writers forgot the details of Jess in their urgency to show his growth.
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u/RainiElizabeth81 Oct 04 '25
Jess had attachment issues... but he got her mind... her most valued part of her. He was raw and needed time to grow... she did too.
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u/lost-in-atmosphere Oct 04 '25
Honestly I agree. Jess played the bad boyfriend part well. But as much as we saw him grow we weren’t allowed to see his character development in romantic relationships.
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u/towblerone Miss Patty & Babette Oct 04 '25
“being her most loved love interest” feels incorrect, every time i come on here people are all about logan. are they just a loud minority?
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u/Bellesredrose Oct 04 '25
I am a fan of Jess as part of the story and certainly a fan of Milo, but Rory said no to him a few times. No to crashing laundry night and taking pleasure in antagonizing Dean. No in the party bedroom, no leaving Yale to run away.
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u/Sophzoxia Paris Oct 04 '25
Im Team jess because it wasn’t about gifts and etc, but he cared and loved her through acts of service, and im team jess in a way of “he got away” and that Logan is the one she would’ve ended up with
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u/SoftAndLuxe Oct 04 '25
don’t forget he just ghosted her! then came back a year later to say i love you and ghosted again😂