Gilmore Girls: Why Rory and Jess were always the endgame couple, explained

Gilmore Girls, the brainchild of Amy Sherman-Palladino, is the one with all the fast-talking, endless coffee, and chronicles the coming-of-age journey of a mother-daughter duo.

The story revolves around Lorelai Gilmore and her daughter, Rory, who is fumbling her way through growing up, dodging love: Dean Forester (tall, nice, honestly kind of a snooze), Jess Mariano (the classic brooding bookworm with a chip on his shoulder), and Logan Huntzberger (rich, charming, kind of a walking trust fund).

Since the show’s first run (back in the early 2000s) and then a Netflix comeback in 2016, people have been talking nonstop about one question: Who should Rory end up with?

When Jess Mariano (played by Milo Ventimiglia) shows up in Stars Hollow, he immediately shakes things up. He is misunderstood, rebellious, and probably smells like cigarettes and library dust. His relationship with Rory is more than just angsty make-outs. It goes deep, with big themes like class, brains, trauma, and figuring out who you’re supposed to be.

Their romance is a mess, nobody is denying that, but there is a pretty loud camp that says Jess is THE guy for Rory. Not Dean. Not Logan. Team Jess, ride or die.

So, here’s what we’re working with:

(1) The writers set up Rory and Jess to be each other’s intellectual and emotional match; you can just feel it.

(2) When they’re together, they push each other to grow up, which is rare in TV couples.

(3) The show is packed with meta-hints and sneaky references that scream these two belong together, if you’re paying attention.

(4) And, maybe most important, there’s all this unresolved, cliffhanger energy, the show never really lets you close the book on Rory and Jess, which keeps the “endgame” dream alive for fans who love a good what-if.

So, that’s the hill Team Jess is willing to die on.

Disclaimer: This article reflects the personal views of the writer; reader discretion is advised.

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Intellectual equals: Canonical evidence and critical reception

Out of all Rory’s boyfriends in Gilmore Girls, Jess is the only one who can actually keep up with her brain. It’s not just fans who say this; the show shouts it from the rooftops, and critics agree.

From the start, Jess and Rory are trading book recommendations and having these nerdy, rapid-fire conversations. Meanwhile, Dean is over here, sweet as pie, but his idea of deep conversation is, like, “I support you, Rory!” And Logan has got the whole ‘rich bad boy’ thing, but he is more about yacht parties than Dostoevsky.

The Jess-Rory chemistry is built on their love for books. Remember that scene in the Stars Hollow gazebo, reading Howl together? That’s not your average teenage date. They’re tossing around references, arguing about novels with actual debates. Dean tries, but his attempts to talk literature are... cringe. Jess just gets her, right from the first moment.

And as Brit + Co points out, Jess isn’t just there to be Rory’s cheerleader; he challenges her. Their banter isn’t just for show; it’s two smart kids pushing each other to be better, which is rare on TV. Usually, the “boy next door” is safe and boring. Jess, though, keeps her on her toes.

It’s not just shippers who noticed. Media and gender scholars have noted the rarity of a teen drama portraying a girl’s intelligence not only as visible but also as desirable. Their relationship breaks the old-school, sexist mold of early 2000s TV couples by portraying Rory and Jess as equals. That’s why so many people still root for them; they’re the real deal, not just another high school cliché.

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Relationship as a crucible: Mutual growth and hard lessons

Rory and Jess’s relationship in Gilmore Girls is like chaos meeting growth. Jess bailing when things get tough, Rory shutting down emotionally, is a teenage thing to do. But that’s what makes their impact on each other so important.

Like, Jess is the only one who says what everyone’s thinking when Rory’s spiraling. He tells her bluntly to return to Yale when she dropped out, prompting a turning point in her character arc. It’s grueling, but it’s exactly what she needs.

Fast forward to Let Me Hear Your Balalaikas Ringing Out (Season 6), Jess rolls back into town, all grown up and author-y, and he is not trying to win Rory back or anything. He’s there to slap some sense into her. He cares, but not in a clingy, pining way. It is more like asking Rory to get herself together because she is better than this. That makes you wonder if he was her best match the whole time.

Flip the script, though: Rory is not just some passive character in Jess’s story. She believed in him when nobody else did, not his teachers, not his family, probably not even himself. She saw the good, the talent, the potential. That little push was massive. Both of them keep showing up for each other at these crossroads. It’s a whole theme: meet, break, rebuild.

But let’s not sugarcoat it, these two were also a walking disaster a lot of the time in Gilmore Girls. There’s one episode (Keg! Max!) where Jess totally disrespects Rory’s boundaries, and fans still argue about whether Jess was just “troubled” or toxic, because he ditched her without so much as a text, picked fights, and could be seriously moody, bordering on straight-up mean.

So, for a lot of people, that’s enough to write Jess off as ever being endgame material. As Bustle outlines:

“He was often moody, aloof, and a bit of a live wire... it’s hard to forget all the misery that Jess put Rory through. From leaving without saying goodbye to Rory, to showing a lack of respect to those closest to her, Jess's innate sexiness was counteracted by his destructive personality.”

That said, if you dig a little deeper, it’s not just about “bad boyfriend” tropes. Their worst moments push both of them to grow up. Their flaws make Gilmore Girls hit closer to home, instead of feeling like some perfect, fairy-tale romance. And maybe that’s the point.

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Storytelling Beyond Resolution in Gilmore Girls

The unfinished romance

In Gilmore Girls, Rory and Jess were never about neat endings. If you’re tuning in hoping for some Disney-style “happily ever after,” Gilmore Girls pretty much laughs in your face. Their relationship is this big “what if” that never fully fizzles out, no matter how many years pass or how many terrible boyfriends Rory cycles through.

By the time A Year in the Life dropped on Netflix, people were still arguing about whether Jess was her soulmate or just another chapter she should’ve closed ages ago.

And it’s not like the writers forgot to give them closure. That tension—will they, won’t they? is on purpose.

Critics from TIME and Screen Rant point out that Amy Sherman-Palladino built her whole brand on unresolved storylines and dangling threads. Jess shows up, older and functioning as a human adult, giving Rory the kind of support she needs at that point. But the romance is still hanging in the air, unresolved as ever. It’s like Gilmore Girls knows some stories just don’t end, and that’s the point.

A Year in the Life and the subtle passing of the torch

When Jess shows up in the revival of Gilmore Girls, he is not some prize for Rory to win, or even the bad-boy heartbreak she needs to get over. He’s the steady voice reminding her who she is when her life’s a dumpster fire. Brit + Co even called him her “guardian angel.”

That last scene between them is a slow-burn, lingering look through the window, Jess watching Rory, maybe thinking “someday.” Gilmore Girls doesn’t slam the door shut on them, not even close. Whether you’re Team Jess or just here for the witty banter, you have to admit: leaving things open might just be the most Gilmore Girls thing ever.

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Patterns in fandom, psychology, and this whole “endgame” obsession

Fandom & how we see stuff

Rory and Jess shippers are detectives at this point, combing through every little line or glance for clues that they’re soulmates destined to reunite. Theories go viral as people break down visual symbolism.

But not everyone’s buying it. You’ll find just as many think-pieces and Reddit rants arguing the magic of Jess/Rory is that they never actually get their neat little ending. The “will-they-won’t-they” is the whole point. Someone on Reddit even nailed it, saying,

“Rory & Jess are platonic soulmates, not romantic ones”

Attachment theory, but make it TV

You know how people root for TV couples who keep screwing up, then maybe get it together? Psychologists say we see ourselves in that chaos. Jess and Rory aren't your standard, sanitized high school sweethearts; they’re the human dumpster fire version, all unfinished business and awkward timing. People love to watch characters fight for “earned security,” meaning they work through their baggage instead of magically being perfect together.

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The messy bits: Flaws, toxicity, and why “perfect” romance is overrated

Jess is not exactly boyfriend of the year

Nobody is pretending Jess is some dream guy. He ghosts people, gets jealous, shuts down emotionally, and there’s one truly cringe moment with consent. Fans and critics call him out all the time. But Gilmore Girls never tries to sell Jess as Prince Charming. He’s a work in progress. Rory might spark some of that growth, but she’s not his magic fixer. He’s gotta earn it, or he doesn’t.

Rory’s not winning relationship awards either

And let’s not pretend Rory’s perfect. She cheats on Dean, barely opens up to Logan, and half her issues come from her family drama. By the end of Gilmore Girls, she is a mess herself. If Jess is her “endgame,” it’s only because both of them are still figuring themselves out. Not because they’re some storybook couple.

Why we kinda love unfinished endings

A lot of TV scholars argue that the best love stories on TV don’t wrap up with a bow. The unresolved stuff is where the magic lives. Rory and Jess never really get closure, and that’s why people are still talking about them. The “what if” is sometimes better than the “happily ever after.”