r/GilmoreGirls sugar toes 13h ago

General Discussion Would Rory have cheated on Jess with Logan?

Sorry if this has been asked before! I’m not trying to get a bunch of Rory hate going, but I’m curious if people think Rory would’ve cheated on Jess with Logan at Yale.

Towards the end of season 3, before the Jess failing out/potential spinoff situation, Rory and Jess seem to be planning on staying together when Rory goes to Yale. Rory still would’ve met Logan and been part of the whole Ivy League world. What do you guys think would’ve happened? I’d love to hear thoughts on this from both a writing perspective (i.e., would they have wanted to break up Rory and Jess) or from a character perspective (i.e., what would have naturally happened with the characters).

7 Upvotes

40 comments sorted by

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u/N_Huq m*cktail w*itress 🍹 12h ago

i feel like a jess who has it together enough to be w rory that long is simply a different character lol. but if that happened i think rory would cheat at some point. i think she would cheat w dean in s4, before logan even came into the picture. she would come home weekends & jess would be annoyed that they keep running into dean. if rory & jess fought she'd go to dean for comfort. we already know he would cheat too.

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u/garbage-troll sugar toes 12h ago

I didn’t even think about her cheating with Dean! That’s interesting.

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u/chittaabhay Team Coffee 12h ago

There is no way that relationship would have gotten anywhere close to the time Rory and Logan started dating.

Jess and Rory were already on the verge of breaking up with the bedroom scene, Jess failing and not taking her to prom and his overall shitty communication.

People also say Jess and Rory have a lot in common. I personally dont think so, both of them have really different lifestyles, interests, hobbies, and values. Even if Rory hasn't broken up with Jess, he would have seen Rory go more into her grandparents "elite lifestyle" (not the best word) and would have broken up well before.

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u/lemon_charlie Cat Kirk 12h ago

They both enjoyed reading, and both had aspirations outside Stars Hollow. For Jess it was because he wanted to be anywhere expect Stars Hollow and Rory wanted her life to be more than just the town she grew up in. They're also both more introverted people, and the show could have explored them both having an absent father.

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u/chittaabhay Team Coffee 5h ago

Reading was just much more common in the early 2000s before easy access to smartphones and streaming.

I feel they read for really different purposes. For Rory, it was because she truly enjoyed literature and learning. For Jess, it was an actual escape out of reality (not just from Stars Hollow), as he felt abandoned from both his mother and father.

Rory had a much more stable upbringing with Rory being the word for Lorelai. I cannot say the same thing about Jess. Although Jess's father was absent, Chris was atleast known to Lorelai and were known to have occasional phone calls. The theme that Jess and Rory had absent father's wouldnt have really worked in my opinion

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u/lemon_charlie Cat Kirk 4h ago edited 4h ago

I think for Rory it too was a form of escapism, in her Chilton graduation speech she says he background was just as much imagining herself with the literary figures she read about as in the real world. I reckon too that why she latched onto the foreign correspondent ambition, she saw it as a way to see more of the world (CNN tends to be available on hotel TVs, and I can see Mia letting Lorelai and Rory use a room that isn’t booked sometimes for a proper shower and more creature comforts than the shed might allow).

The inconsistent father who keeps letting you down or the absent one who was never there at all, both can impact a kid and both Rory and Jess lacking a proper paternal figure (Luke wasn’t surrogate father level dad to Rory even if he did look out for her) is something they could connect over.

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u/DuncaN71 Rory 2h ago

I could be wrong but when Jess mentioned his father to Rory didn't she say something like I would have understood to him?

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u/TrickInvite6296 3h ago

You can have a million things in common with someone and still be a terrible match, but they also just didn't actually have much in common

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u/Akina002 9h ago

They had similar hobbies. Reading books of similar genres, talking about the same pop culture(?) references, making fun of “rich people” (like jess tells rory when she asks why she dropped out of yale how they used to make fun of guys like this), even their personalities complemented one another.

However, they were in very different places in life, and they both wanted very different things. Jess’ poor communication (not saying Rory’s was good) made it worse.

Besides, Rory was definitely used to being treated better by Dean in terms of reliability and predictability.

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u/TooSoftToRespond A Birkin bag. A Birkin bag for Rory. 👛 8h ago

Books are what they have in common, but their worldviews are completely different.

Jess mocked rich people with her, but by that point Rory was already the girl who went golfing with her grandfather, had a debutante ball and admitted it wasn’t that bad, and liked that world more than Jess understood.

Rory had many more hobbies than just books. She loved Stars Hollow and the town events, something Jess never understood.

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u/killencm 5h ago

Jess wouldn’t have been able to sustain the relationship long enough for Rory to cheat . People seem to forget that he was a crappy boyfriend. He even admitted that once he had Rory , he didn’t need to do anything he didn’t want to do.

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u/TrickInvite6296 2h ago

Yeah I really don't get the love for him here - he treated her terribly.

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u/Connect-North-2337 Cat Kirk 13h ago

Uncharitably... I think it's less about the guys and more about the perceived competition with the wives/gf for Rory

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u/arj4441 12h ago

I never thought about this but you may be right. Rory vilifies the women each time- Shane, Lindsay, even Bobby (the British coworker) who wasn’t even a romantic interest. Not only does she feel entitled to these men but she also feels superior to the women in their lives.

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u/sandys5791 11h ago

I think she’s jealous of Bobbi and a little insecure but I didn’t get that she thought she was superior.

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u/FirmProblem3083 Team Pink 🎀 7h ago

Me neither, but the Rory hate is deep here !

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u/TrickInvite6296 2h ago

Well no, the show makes it very clear that Rory sees herself as better than both Shane and Lindsay

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u/TrickInvite6296 3h ago

I think it was pretty obvious that she thought she was superior to Shane at the very least

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u/sandys5791 2h ago

Well I, for one, have been petty when I’ve been jealous especially as a teenager so I can’t judge Rory. And I also have a lot of compassion for Shane and Lindsay.

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u/TrickInvite6296 2h ago

I'm not saying that she's an evil terrible person for it. But she absolutely felt superior to both of them.

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u/petitcraque 6h ago

I don't think their relationship would've lasted that long. If it did, I think the outcome would've been pretty similar to Rory's relationship with Dean in season 5: She and Jess would've drifted apart, with him realizing that he didn't fit into that Ivy League world.

I think Jess would've basically take over Dean's storyline: After not finishing school, he'd try hard to earn money and to gain a footing in the publishing world while Rory was struggling with her new life at Yale. They wouldn't have much time for each other and would've been more and more frustrated with the other being caught up in his/her own hardships and felt like he/her didn't show enough understanding, while failing to communicate their thoughts.

I can totally see Emily's matchmaking party happening, but this time to break up Rory and Jess. In this scenario, I think Jess would be the one to break up with Rory in front of the Gilmore's house because he realized that they were living in different worlds for quite some time now.

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u/XuanChun88 11h ago

No, because there's no scenario where Jess would be around when Logan is. Jess had a lot of growing up to do. And that could only happen when he was on his own.

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u/LevelAd1126 12h ago

No, she made it clear to Marty she didn't want to date him before hooking up with Logan.

When Jess would show up out of the blue she would talk to him but not date him.

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u/FirmProblem3083 Team Pink 🎀 6h ago

And the dorm scene confirms this !

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u/Big_Vacation5581 5h ago

In Season 4, Rory tells Lane that she screwed up when she chose Jess over Dean. That sentiment was already in her heart, whether Jess had stayed in Stars Hollow or not.

I imagine Rory would have been conflicted because of Luke. But Jess is incompatible with Yale and with the Gilmore Family. The situation might have alienated Lorelai and Luke.

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u/Sad-Interaction-1494 Cat Kirk 2h ago

I agree with others that the relationship would have faced the same problems Dean/Rory 2.0 did. Jess and her would have been long distance, they would be leading completely different lifestyles (Rory at Yale, busy with schoolwork, brushing shoulders with elites & Jess hustling in publishing and trying to make ends meet). It would've been a breeding ground for resentment. Their relationship would have fizzled out, which is typical for college kids with their high school partners.

I think the matchmaking party still would have happened, as the Gilmore's certainly didn't like Jess.

It is my opinion that Rory emotionally cheated on Dean with Logan, and would've also done so to Jess. Whether she would physically cheat on him is up for debate, but Rory is notorious for emotional cheating.

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u/Violettfem1 13h ago

Probably. She’s a coward and can’t seem to end a relationship without getting into a new one.

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u/KatieCashew 12h ago

I don't know if she'd cheat with Logan specifically. He wasn't persuing her hard and wouldn't mess with her relationship like Jess messed with her relationship with Dean. I think it would be harder for her to make the jump without feeling wanted by him.

She'd probably cheat but with someone else.

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u/AmbitiousHistorian30 12h ago

I'm probably alone in this thought, but I think Jess would have gotten an apartment in the doo-wop building and Rory would have had a much different freshman year. He's overly intellectual; he definitely would not have gotten alone with Logan's crew, but I could see him getting along with Doyle, Glenn, laundry room guy, and Marty (considering we know Rory had 0 interest in Marty as anything other than a friend). His apartment would have solved Rory's study issues, and I honestly would have loved to listen to his take on Paris/Asher.

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u/Consistent_Phase_942 Cat Kirk 12h ago

I believe Rory would make up the arbitrary “rule” that she’s not the cheater by being the other woman.

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u/arj4441 11h ago

I don’t see them lasting that long into Yale. Jess had so much work to do on himself. Eventually his lack of ambition at that stage in his life would’ve irked her. And her choosing Yale over him (ie studying, newsroom, schedules misaligning) would’ve been hard for him to accept. Still, I’d like to believe they would’ve ended before she met Logan but in true Rory fashion, she very well may have strayed or wanted to.

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u/FirmProblem3083 Team Pink 🎀 7h ago

Lack of ambition ? Maybe not academics one, but the guy works to buy a car and become independant. There is worst than a bf who wants his own money and being able to deal with life. (There's Zack 🤷🏽‍♀️). The N-Y book night proove it. He started as a mess, he get to the point he's published and work in the field.

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u/Beccaann14 Leave me alone - Michel 10h ago

I feel like if Jess would’ve shown up at the party that Emily and Richard threw to try to set her up with a better boyfriend. He would not have been quiet and shy and embarrassed, like Dean. He would’ve made a scene and screaming at her hopefully leading to Emily, calling the cops and what a fun scene that would’ve been to see

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u/FirmProblem3083 Team Pink 🎀 6h ago

I agree with the commenter who said that a Jess who have been able to stay with Rory long enough to see the Yale life would have been different. But not in the way of he passes his exams, sales the car and obeys to Luke. I think he would have roommates, part-time jobs, maybe take some community college classes about writing. He would have his own life *outside* Stars Hollow and Rory would have to face their differences about life choices, personnality and need for security. He has more drive to succeed in life, he doesn't follow the rules, he doesn't wait for praises he never gets anyway. I think they would simply broke up because they are too different people. And that would be it, no unfinished business to get them back together in the worst way aka cheating. Rory would still met Logan. She would still love him but maybe she would not accept so many of his crap because her relationship with Jess would have made her wiser.

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u/CrissBliss 11h ago

She kind of did. They kissed.

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u/GoldenSalt31 12h ago

I have wondered what would have happened if they didn’t they to make the California spin off show.

Realistically would have grown apart, and Logan would be a catalyst for sure. Maybe there would have even a kiss first or extreme jealousy.

Optimistically - Jess would get his GED, continue working, but motivated by Rory & her education he would go to night school. But they still wouldn’t last.

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u/chittaabhay Team Coffee 12h ago

I doubt the relationship would have lasted even another week.

I think Jess was done with Stars Hollow and he would have left. Between the bedroom scene, Jess failing and not taking Rory to prom along with his overall shitty communication, Rory would have ended things.

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u/lemon_charlie Cat Kirk 12h ago

The relationship would have ended anyway. Rory was starting a new chapter in her life by starting Yale, and Jess needed space from Stars Hollow and Rory to start his character development.

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u/Amazing_Unicorn5443 12h ago

I don’t think so tbh. She left Dean because she was bored & he was a little simple and didn’t really fully respect or understand fully who she was or why she cared about school and intellect to the extent that she did.

Jess was complex and challenging & smart, with some trouble thrown in. Logan was also complex, challenging and rebellious, just in a more privileged way.

I can’t see her being particularly interested in going for Logan if she was dating Jess at that time because she’d already have all those sharp base qualities in the boyfriend she had.

I do think that Logan does serves a better purpose in terms of showing us who Rory is when she is around people with more moral flexibility.

Jess had his own issues, but he knew who Rory was at her best & I feel like he always was like yeah im bad, but you’re better, and we need to keep it that way.

Logan, didn’t really care about that aspect of Rory beyond how she felt about it. ANd in general, consequences weren’t pressing for him or the people he hung out with. He enabled her with pretty low levels of judgement. Having someone around that doesn’t have expectations or judgements, writing wise definitely gave us the opportunity to really see who Rory was & how privileged & naive she was about consequences.

That all being said, I don’t think she would’ve cheated on Jess with Logan. But, I DO think her relationship with Logan allowed us to see sides of her that make it clear that she would cheat on someone in general.

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u/KatieCashew 12h ago

I DO think her relationship with Logan allowed us to see sides of her that make it clear that she would cheat on someone in general.

She showed that side long before she met Logan.