Even in 2022, Gilmore Girls fans are still debating who Rory should end up with, especially since the A Year in the Life revival leaves her story more open-ended than ever. Perhaps the largest section of the fandom believes in the pairing of Rory and Jess.
Even though these two haven't been together since season three, it's easy to see why it's hard to give up on the potential of their coupling. From the beginning of their story, all the way through its current ending, Gilmore Girls establishes these two as each other's perfect equal and possibly each other's soulmate, too.
"You Looked It Up."
Rory Gilmore - Season 3, Episode 18
Rory's decision on which college to attend is a major storyline in the third season of the series. It also represents a major milestone in hers and Jess's relationship, since it's something that could potentially change their status as a couple.
This is something Jess is all too keenly aware of, and even something he is able to surprise Rory regarding. When he lets Rory know that Yale is 22.8 miles from Stars Hollow, she is stunned, repeating, "you looked it up" over and over again, as she is genuinely touched by his sweet gesture and forward-thinking outlook.
"You Know, Ernest Only Has Lovely Things To Say About You."
Jess Mariano - Season 2, Episode 13
Unlike in her first relationship with Dean, where they didn't have anything in common, Rory and Jess connect due to their shared love of literature. Even if they don't agree on the same authors, there is a like-minded intellectuality to their conversations and their flirtations, too.
During the memorable picnic basket auction episode, they discuss the author Ernest Hemingway, of whom Jess is a fan and Rory is not. "You know, Ernest only has lovely things to say about you," Jess teases, and Rory is too enamored to disagree.
"Why Did You Come Here? I Mean, You Ditched School And Everything. That's So Not You. Why'd You Do It?" "Because You Didn't Say Goodbye."
Jess Mariano And Rory Gilmore - Season 2, Episode 21
Out of all of Rory's relationships, her relationship with Jess is the only one that keeps starting and stopping over the years. When Jess is first sent out of town, Rory takes it upon herself to seek him out in New York because she can't accept that this is it for them.
"Why did you come here?" Jess asks her as they prepare to part ways again. "I mean, you ditched school and everything. That's so not you. Why'd you do it?" Rory has always been a rule follower, but Jess brings out a different side of her that she can't let go of. "Because you didn't say goodbye," she explains, and that truly says it all.
"I Know You Better Than Anyone."
Jess Mariano - Season 6, Episode 8
Jess and Rory are positioned across the series as each other's foils. Their time together as a couple is relatively short-lived compared to the series' overall length, but their role in each other's lives, as friends and confidantes and more, extends well beyond that.
That they are able to build a foundation before their relationship, first as somewhat rivals and then as good friends, allows them to be able to call each other out at pivotal moments. When Rory drops out of Yale and is floundering in season six, Jess is the only one who is able to get through to her. "I know you better than anyone," he boldly claims, and in many ways, he just might be right.
"You Can Do Anything You Wanted. You Can Be Anything You Wanted."
Rory Gilmore - Season 2, Episode 19
Just as Rory and Jess challenge each other, they are also unflagging in how they believe in each other. Rory in particular is a shining example of this, as she is one of the few characters who believes that Jess is capable of more than the low expectations Stars Hollow has set for him.
"You can do anything you wanted. You can be anything you wanted," she tells him in season two. And that deep belief in his potential never wavers as long as they are in each other's lives.
"I Don't Wanna Talk To Anyone Else. I Don't Like Anyone Else."
Jess Mariano - Season 3, Episode 19
One criticism that people make of Rory and Jess's relationship is that he is hated by everyone else in her life. It could be argued that no one really makes an effort to like him after a bad first impression, but it's also true that Jess is limited in his interest to be social with anyone else.
He comes out and says exactly that in the season three episode "Keg! Max!" after agreeing to go to a party with Rory: "I don't wanna talk to anyone else. I don't like anyone else." But he is willing to go along with Rory's desire to be social and allows himself to be brought into her world, even when it doesn't come naturally to him.
"I Could've Been A Contender." "You're Still A Contender."
Rory Gilmore And Jess Mariano - A Year In The Life: Summer
In many ways, Rory and Jess can be described as "right person, wrong time." Their journeys have never lined up perfectly, with Jess maturing later than Rory, and Rory struggling with herself later in her young adulthood when Jess has already figured his life out.
In A Year in the Life, Rory laments her current feelings of failure by quoting On the Waterfront and saying, "I could've been a contender." Without hesitation, Jess assures her, "You're still a contender." No matter Rory's own doubts, Jess never doubts her.
"I Couldn't Have Done It Without You."
Jess Mariano - Season 6, Episode 8
It's a big surprise when Jess returns in season six, not just because he hasn't been around in a while, but because he returns a mature young man who has written and published his first book.
After years of bad behavior and struggling with low expectations, Jess has finally bought into the belief that people like his uncle Luke and Rory had in him all along. "I couldn't have done it without you," he thoughtfully tells Rory when he gives her a copy of his book, and he's probably right.
"You Know We're Supposed To Be Together. I Knew It The First Time I Saw You Two Years Ago, And You Know It, Too."
Jess Mariano - Season 4, Episode 21
Rory's first year at Yale is a difficult one for her in many ways, but it ends in quite dramatic fashion when Jess shows up unexpectedly to try and convince her to run away with him.
He takes things even further than that, passionately proclaiming, "You know we're supposed to be together. I knew it the first time I saw you two years ago, and you know it, too." It was love at first sight for Jess, even if he didn't know it then. And even though Rory turns him down at that moment, it's clear that the feelings may have been mutual, too, given how painful the ordeal is for her.
"It's What It Is, You, Me."
Jess Mariano - Season 6, Episode 18
In a perfect world, Jess and Rory would find a way to be together. Maybe they need to address the years of history and baggage between them before anything new could begin again, and maybe things would look incredibly different now, with Rory expecting a baby of her own at the end of A Year in the Life.
But whatever their future relationship could look like, one thing is clear: it would be a relationship unlike any other coupling Rory could have. "It's what it is, you, me," Jess sadly tells her at the end of season six when their timing is wrong once again. There is so much history between these two that it's not hard to want them to finally find a way to make things work, even now.