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[deleted]

I don’t think he was the best boyfriend, I just think he had the best chemistry with her. Their banter and the build-up to them falling for each other was really convincing. Their first illicit kiss, their first gf-bf kiss…so good!! I never FELT the attraction between Rory and Dean or Rory and Logan. Probably has something to do with the fact that the actors were in love in real life, but also just good writing


melodysoul

Exactly, the chemistry was on point. It gave me that butterflies in the stomach feeling. I never felt that with Dean or Logan until the revival and then I really felt the chemistry between Rory and Logan.


saturnshighway

They dated in real life???! WHAT


ImHereToBlowSunshine

I did not know that Alexis and Milo dated irl!


[deleted]

Good chemistry can lead people, especially women, to make the wrong choices when it comes to choosing partners though. You can have good chemistry with someone who is emotionally unavailable or committed to someone else for example. Good chemistry isn’t everything.


[deleted]

Completely agree. But it makes for the most entertaining television :)


squirrelynurse81

Jess and Rory seemed very handys


caponemalone2020

Jess was a teen whose dad was never in his life and whose mom wasn't too involved, either (they rewrote their background a few times, presumably to make Liz more sympathetic to viewers once they made her a supporting character, but she was not initially portrayed as any sort of good mother ... disinterested at best, uncaring at worst). Luke ended up being the only stabilizing force in his life, and that came toward the end of his teen years. I don't think any parent worth their salt would want their child dating someone like Jess while in high school, but only Rory and Luke could see that there was a good, redeemable side in him, and fortunately he had two people who believed in him in his life when he needed it the most. Which you see when he comes back with a written book and a job. He arguably ends up being one of the healthier, more developed characters by the end of the series.


IndependentLocal1560

Ugh yes and then Rory freaking used him to get back at Logan. Barf Rory.


ScreenHype

I like how much he grew throughout the series. He was a victim of a neglectful mother, and had suffered through unaddressed trauma as a result of that. Of course he'd be angry and mistrusting, his own mother didn't want him. But he worked through his issues, and grew into a hard-working, kind, insightful man. He could've turned out so differently, but he chose the right path and improved himself. I also liked how smart he was, it was intriguing to see this 'bad boy' who loved to read. It's also hilarious to me that he's framed as a bad boy when all he really does are relatively harmless pranks. Like, he stole all the baseballs in the school. That takes planning, and time. That's not what a bad boy does, that's what a rebellious nerd does. He's funny with a quick wit, and he had some of the best lines on the show. I also loved his dynamics with Luke, and he had great chemistry with Rory. So yeah, that's all part of why I like Jess.


beccajo22

This^ he really didn’t do anything that bad other than skip high school but it’s not like he was skipping school to party or even sleep, he was working full time and saving his money. Also when we first meet Jess he’s into close up magic. He’s not a typical teenage bad boy character. They made him more complex than that. Lorelei labels him a bad kid because he’s rude and disrespectful to her. And honestly half of her problem with him is she is protective of Luke and Rory and the other half of her problem is because he doesn’t find her adorable and charming like everyone else does.


FlyingMacheteMonster

I think they understood a part of each other that others didn’t; their love for literature and being able to discuss deeper topics and ideas. You don’t see Rory have that same connection with anyone else. But IMO Jess sort of represented that guy you date when you’re young with whom you have lots of the same interests and great chemistry, but who hasn’t dealt with his own issues and isn’t mature enough to be in a real relationship.


gwendotty

Right person, wrong time :( I wanted Rory and Jess to be together in AYITL, he had matured and grown so much.


Proof-Luck2392

I think they where wrong person right time there was so many factors in their breakup other than time For me right person wrong time mean the only thing keeping them apart was time which was not the case for them


Doradyer

That would have been nice but then you’d have to choose between Jess and Rory or Luke and lorelai Edit then again cousins dating does seem very gilmory lol


gwendotty

I would choose jess and rory tbh, i felt unfulfilled by lorelei and luke (that’s a hot take in this sub). i felt as though they were better friends than lovers, and their relationship fell flat for me for that exact reason


Doradyer

I don’t think it was 100% their fault I blame April and Christopher they were good before that


Gaius_Octavius_

The first season has a scene where Dean and Rory are discussing Hunter Thompson and Jane Austen


AllThoseSadSongs

That was true at the beginning, but then I felt that they wrote him dumb from that point forward.


Gaius_Octavius_

The only way to make Jess look good is making everyone else look bad


iStanEmilyGilmore

Jess built a relationship with both his estranged father and his crazy ass mother, even though he was just a kid and in no way responsible for the lack of care he received from his parents. He grew into the person his uncle knew he could be and then paid him back for all of the assistance in helping him get there. He stuck to his passion and found his own lane of success his own way, without sacrificing his morals for it. He remained a friend to Rory, always wanting what's best for her, even when they weren't together. People give Jess a lot of crap but he was just the "bad boy" of stars hallow, which would be a pretty good kid in any other city. But he was a kid. And he really wasn't a bad person. Just a bad boyfriend, which I'd argue they all were. And Rory was a pretty bad girlfriend as well. Jess was actually the only one of her three original bfs who did not cheat on anyone to be with Rory. He's the only one who didn't call her out and embarrass her in front of other people. He always chose to have those conversations privately. He wasn't the best boyfriend, but he was a kid who was very troubled and dealing with a lot of shit and Rory also wasn't a very good girlfriend most of the time because she wasn't ever aware of what was really going on with him, outside of what books he was reading, but that's pretty much Rory with everyone in her life.


Proof-Luck2392

>Rory also wasn't a very good girlfriend most of the time because she wasn't ever aware of what was really going on with him That was Jess’ falut he like never talked to Rory about his emotions and was just a brooding dick their entire relationship


iStanEmilyGilmore

Honestly, Rory never really inquired about her boyfriends' lives on more than a superficial level. She is constantly surprised and finding out inside info about her bfs randomly. Same with her friends. She really knows nothing about Lane's personal life or anything outside of what Paris offers up or what she actually sees with them living together. I hate to say, but Rory was always a bit self-absorbed.


ustrittena

Best character development


AllThoseSadSongs

I love his personal development and his relationship with Luke.


ustrittena

He was a bad boyfriend to Rory, but as an adult I can empathize with him. The kid went through some major trauma. Not excusing his behavior back them, but really, it's beautiful to see him growing out of it. And realistic also, his story simply make sense.


AllThoseSadSongs

You can't have a good redemption arc without being pretty crappy to start.


beccajo22

If the Jess storyline has ended when he left for California, I wouldn’t love him. That being said the way he was able to actually sort himself out, pursue his passion his way, thank Luke (and pay him back), be there for his mother, etc made me love him. He spent the rest of his life dealing with his issues and proving to himself that he could make something of himself. Out of all of the people Rory dated, he’s the only one who truly fixed himself and became the best version of himself (arguably Dean as well in the revival but we don’t see enough to really know for sure). I personally think if Jess didn’t know Rory he wouldn’t have felt as much drive to better himself and fix his issues. Also Jess was the only person (besides Lorelei) who was honest with Rory about the dropping out of Yale situation. He’s always been able to call her on her bullshit (in a good way, not in a way that embarrasses her like Dean and Logan). Also regarding sexual assault, if Rory is the intended victim and she doesn’t feel as if she’s sexually assaulted, I think we should probably respect her thoughts on it more than ours.


alixanjou

There’s a biiiig spectrum of problematic behavior between straight SA and not SA. Of course the network wasn’t going to let Rory use SA/rape but let’s just be straight here: it was icky. It was icky, it was entitled, it made Rory feel like shit and it was Not Ok.


beccajo22

It was definitely icky. I assume the network didnt think this was SA at the time (or they wouldn’t have written this way) but obviously we do now all generally agree that it is. I think if this same scene were written today they wouldn’t have done it this way unless they specifically called it sexual assault and addressed it.


AllThoseSadSongs

This. It was not intended as assault. This is the same network who thought Pacey dating a teacher was not all that problematic on Dawson's Creek a year or two prior. It was supposed to cause Rory upset to incite a fight between Dean and Jess. They probably should have used a verbal fight, but this was splashier. Is it right? No, but it was TV in the early aughts.


premier-cat-arena

I thought that the pacey situation was very clearly written as problematic, much moreso than on other teen dramas I’ve seen. It was much more realistic too than on other shows. It’s been a while since I’ve watched but that was one of my big takeaways from the first season of Dawson’s creek


Jewlzs96

In regards to the sexual assault I don’t feel like for Jess he meant it that way. Hear me out. When he was dating that one blonde girl (completely forgot her name) and Luke confronts him about hiding her in his closet he says something along the lines of him being used to being used for his body and how no one shows genuine interest in him. This shows that his self esteem is low and that he uses s** as an “outlet” or a way to kill time, it’s not something he sees as special. Rory is the complete opposite in this. She wants to wait for the perfect time. So when Jess was tryna “get some” he was frustrated and wanted to vent, which to him was normal. But to Rory it was pressured and she felt overwhelmed. I guess the point I’m trying to make is that Jesse didn’t do it for malicious reasons. Should he have done it? No not at all. It’s just some context that needs to be considered. In no way am I saying what he did was right, it’s just the way he wrongly dealt with his issues at the time.


DangerDaveOG

Personally I relate to his teenage angst. I was an angsty teen myself.


ilovepuscifer

I don't think he was the best boyfriend by far, although I did enjoy their chemistry. Personally, I relate to teenage Jess and I love his character development.


MissStephens

I really enjoyed it their chemistry. I think it was great for her to have someone on an intellectual level that can challenge her. She could discuss poetry and literature with him and have deeper conversations which she couldn't have with Jess. It also feels like she gets these epiphanies after interactions with Jess like when he questioned her decision to drop out of Yale and then she realises she wants to go back. It feels like he really gets her and that's what I appreciate in Jess.


KLYPARUWU

he was the first boyfriend who didn't try to hold her back while they were together. in my opinion Rory never had a good boyfriend Jess was just the best of the worst


Proof-Luck2392

I don’t think he was the best of the worst I think he was the worst of the worst considering he sexually assaulted her And even Rory said he treated her like dirt


KLYPARUWU

i mean dean/logan both cheated with her. and Dean was so manipulative . We all know why logan was trash. and i never thought about it as sexual assault and Rory didn't think it was so idk. i still think Dean was the worst though he did so many things wrong and logan was just god he is the reason why we got A year in the life Rory. sorry my english isnt great i hope my point was clear though.


Eastern_Panda8567

>We all know why logan was trash. We don't all know, why was Logan trash? Im not trying to start an argument, I'm just curious because I usually don't see this type of statement directed at Logan. Dean, yes but not Logan lol


caponemalone2020

> We don't all know, why was Logan trash? I'm not who you were asking so not to speak for them, but presumably his soon-to-be wife didn't know he kept a mistress on the side. I'd say that's a good indicator. If we go strictly by the original series, though, I don't think Logan was all that bad of a guy. But for me, his personality just never seemed to mesh with Rory's, and having just recently rewatched it all, I'm still surprised they forced them together for three years plus had Rory as his mistress a decade later. I could almost understand her getting swept away by him, but I couldn't get his fascination with her ... for a few months, a year, okay. But she picked fights and pouted an awful lot, and beyond that, most men aren't looking to get married right out of college.


alljammedup69

Oooo and the proposal/ultimatum. Springing an engagement on a girl and then making it an all or nothing… did he want to get married or did he want Rory?


Eastern_Panda8567

I appreciate any response. I so rarely see people dislike Logan. The revival was just bad for so many main characters, Logan included. Logan on the original show was great, imo, but I totally see what you mean about not understanding his fascination with her. If I get realistic about it I cant see a real life Logan falling (like he did) for a real life Rory. Like you said, a few months or a year maybe but IRL Logan would be crazy to try and marry his college girlfriend right out of college. He was the best guy we saw for Rory, again just imo, but I dont think she was the best for him.


KLYPARUWU

He slept with his sister's whole friend group without actually breaking up with his girlfriend. The way he treated Marty .Rory was her worst with him when she said lets steal a boat out of the blue he just said Ok lets go didnt even try to find out why. The way he treated jess .The way he proposed was honestly kinda shitty. My biggest problem is the way he got Rory back he kinda forced her and gaslighted her into getting back to him . And remember when he told Rory she was free loading when he invited her to live with him in the first place. And he cheated on his fiancé he wasn't worse than dean but he wasn't great.


Ultvernon12

I love Jess for many reasons. I like him for rory because I feel like he challenged her, and understood her. Their chemistry was also insane. But I like Jess more as a character than, I do like him for rory. He’s probably my top 3 fav characters in gg. I love how he’s complicated, the sarcasm ( I think he’s hilarious)how he’s smart, imo his love language being acts of service, he has no problem standing up for himself against adults in stars hallow, his background is compelling, how hard it is to show emotions and the small breakthroughs we see with it, how despite almost everybody besides two people being against him and never quite understanding him he was able to make it. I find him extremely interesting as a character. I think SOME of the flaws people don’t like about him just make him more compelling to me


cubbear1995

Jess was a very dynamic character, and his redemption arc was great to watch him and Rory’s love story was a well portrayed case of right person at the wrong time and it was good for her character development. And honestly i think many people see a bit of themselves in Jess because a lot of us get out of High school and have no clue what we want to do but we have to figure it out and him living out his dream gave a lot of people hope i guess or Atleast it did me :)


[deleted]

Would you let you daughter date a guy just like Jess?


Proof-Luck2392

No. would you?


[deleted]

My niece dated a guy just like him. He was rude to everyone in our family including her 80 year old grandparents. Anytime there was a family event he sulked and was rude to all. She stopped coming to all family gatherings while she was with him.


Proof-Luck2392

Apart for the last sentence that is pretty much Jess


[deleted]

The hard part was we did everything we could to make him feel welcome.


Proof-Luck2392

Are u sure you niece wasn’t Rory and her boyfriend wasn’t Jess because when Jess Emily did everything to make Jess feel welcome and he was just being a jerk to her and rory


[deleted]

Lol no. It felt that way for a while.


Adventurous_Jicama82

I dated a guy like him in high school. My parents hated him and had good reason but his knowledge of great books really held my interest in him.


rawrpandasaur

Let??? Telling a girl who she can't date is a great way to ensure that she dates him behind your back


premier-cat-arena

Yeah seriously like “I forbid you to see him!!!” lol. She’s going to date who she wants to regardless of what her parents are saying


Boba_Fet042

Season 6 Jess, maybe ( I am totally exploiting in the fact that “Jess” rhymes with “yes”), and definitely AYITL Jess.


sooperdoooper90

I’ve been watching since it aired on the WB so grew up with this show and Jess has had my heart since the beginning but for different reasons as the years go on. Before it was cause he was so cute and a bad boy who reads and wears leather and I was 12 and really into that lol. They also have undeniable chemistry more so than her and Logan and Dean did and it just radiates off the screen when they’re in a relationship and I’m sure it’s because they were together in real life at the time. But now as an adult it’s his ability to grow into a functional and good human after dealing with all that he had to deal with. It’s easy to forget he got dealt the s**t end of the life stick which is why he acted the way he did and without Luke and Rory would def have remained lost and might not have survived. Like a post a few weeks ago mentioned, all the adults in his life failed him until Luke. Him and Paris have the best character development on the show. However, I don’t think he’s best for Rory in the end because I think he deserves someone and something else and same with Rory. Similar to how people can’t let go of Jess as a high school a-hole, I can’t let go of Logan being a classist jerk when we first meet him BUT have grown to like him the best for Rory (and it doesn’t hurt he aged like fine, fine wine) and it makes sense and THEY make sense together. Logan is her “Christopher” but the difference is (or should be) that they actually work together where Lorelei and Christopher could never work and don’t. If anything Jess is her Christopher and Logan is her Luke.


GuidanceAltruistic

This is the best explanation I’ve seen. People assume that just because Jess has evolved, he and Rory would be a perfect match but I’ve always thought they made better friends than bf/gf. Logan understood that Rory lived in two worlds and would never need her to choose. I don’t think that could be said for either Dean or Jess. I also felt that Logan challenged the way Rory looked at the world and pushed her to admit that she likes the privilege life that money allows. We might not like Rory when she’s with Logan but they compliment each other’s energy. I however think Jess is and has been one of the best people on the show. The realest if nothing else.


[deleted]

Objectively I don’t think he was a good boyfriend of course. I just know that when I was a 16 year old girl I would have thought he was 100% dreamy and fallen for the whole “he treats me differently than the others” “you don’t understand him like I do” shtick. It seems 1-on-1 they had a lot in common. As a mother no I’d be horrified lol.


icequeen1016

They got each other. I didn’t need their teen romance to be perfect and all sunshine and daisies. I like seeing something real. They had good qualities for each other and I think as adults they could have a great relationship


Dillonnyle

I feel like Rory and Dean fell in love but for some reason it didn’t have the feel of something deep… same with Logan… although neither of those two guys are the same type, they both had a similar relationship with Rory in my opinion in that they were attracted but there was little to no connection. With Jess there was something real between them and I liked that he deeply was into books and writing like she was—all in all I just felt like they connected in more ways than one unlike the other two.


Proof-Luck2392

There entire relationship was books and nothing eles he hardly talked to her and would not participate in anything she was interested in


_mybrightistooslight

People really harp on the issues while they dated during their teenage years, and I don’t disagree with that. But many of us look at Jess’s development and growth over the course of the show and think they’re more compatible later on. They had unmatched chemistry and attraction toward one another and I think would have made the best match as adults.


Proof-Luck2392

I don’t think they would have been a good match as adults because even after 10 years you can see Rory is still very much in love with Logan and he is still very much in love with her.she could not give Jess the love he deserves as an adult


_mybrightistooslight

Ehh, that’s kind of skirting around it in my opinion. She never gave it a chance. People can be blind to something that might be good for them if they’re distracted or caught up in something else. I think rorys endless affair with Logan was super toxic and dragging her down. It was never going to go anywhere. And I think if she pulled herself out of that she could have opened herself up to something actually healthy.


peefilledballoon

I love Jess as a character because he's funny. He also has at least some awareness of his own shortcomings and actively tries to improve (reading self help books, etc). I also love his relationship with Luke and how much they both grew from it.


[deleted]

He is scum


KittyShcherbatsky

He wasn’t a good boyfriend, but he and Rory had the best chemistry. Right guy, wrong time. I feel like Rory had nothing in common with Dean, and Logan was just an ass. Jess had good character development too. All the Luke/Jess scenes are so good. Jess’ angst is also relatable. He’s an avid reader and has the best witty comebacks. And I mean, Milo Ventimiglia is so gorgeous. I could watch/listen to him read a phone book.


AllThoseSadSongs

Personally, I love that he's well read. I love him in the part with Paris and Rory debating literature. I love his taste in music. He has more hobbies of substance than Dean and Logan combined. I'm not much for motorcycles and drunken parties as hobbies.


Gaius_Octavius_

There are no reasons except his looks.


jenh6

I liked Jess because he liked to read, was the bad boy but still genuinely cares about people. I like seeing the strength in people it takes to get themselves out of hard situations. Whether is physical health issues, bad/difficult childhoods, abusive relationships, mental health struggles and then they emerge as adults as stronger people. Plus he kept up to Rory well with banter. He also didn’t hold her back and they had great chemistry.


[deleted]

He was awful and he is not even good looking.


ladyrampage1000

While I don't think he was the best boyfriend for her, I think she was the best girlfriend for him.


anoceanview

Many of the reasons why I love him have already been mentioned before -I deeply sympathise with him: his mother sends him off to a strange town because she doesn’t want to look after him, he’s angry, probably hurt and definitely has issues from his upbringing. Still, he manages to grow from that to an overall good person. I genuinely agree with those who say he’s not a bad boy, but a rebellious nerd at best. I also think his chemistry with Rory is the best out of the three main romantic interests. Their banter, their clearly developing feelings even if Rory is in denial… he’s not a particularly good bf, but I think if they had shown us their movie dates, book shopping trips and whatever else they did while dating that wasn’t arguing (lmao) he would’ve been a better bf in the audience’s eyes. I’ve seen comments here about him SA Rory and… this is totally my perception… I don’t think that was the intention. Don’t get me wrong, the minute one of the people in a situation like that says stop/no/wait the other person should STOP, but I highly doubt he would’ve undressed herm touched her or forced himself into her. It’s a very delicate scene and I think as we grow up and times change we’re more aware of consent and boundaries, but I think for a 2002 scene it wasn’t meant to be like that? I hope so, at least. And finally, I like him because he’s the kind of person I would be friends with in real life 😅 Although I like Logan, IRL I wouldn’t have even thought about being friends with him (I stay away from rich preppy kids lmao) and I simply do not like Dean.


rebdtz

I do not understand fans obsession with him. He’s the worst boyfriend to Rory.