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Their Story

Jess Mariano, detached nephew of Luke Danes: forced to leave New York when he gets into trouble and sent to Stars Hollow by his mother Liz so that Luke can "straighten him out." He's smart-mouthed, monosyllabic, and rebellious. Pair him with the innocent, blue-eyed, Stars-Hollow-native, straight-A student Rory Gilmore and you've got yourself an OTP.

Lorelai: Oh, your nephew's coming to visit.
Luke: No, he's coming to stay.

When Jess first arrives in Stars Hollow, he wants nothing more than to go back to New York and escape the small-town insanity. But when he comes into contact with one Rory Gilmore, his perspective changes, if only slightly. As time goes on she finds herself spending more and more time with the quiet, brooding diner boy who won't ever be seen without a book in his back pocket.

Lorelai: So, you and Jess aren't friends?
Rory: Well, yeah, we're friends.
Lorelai: Uh huh.
Rory: I mean, we’re not good friends but we’re friends. We’re friendly. But that doesn’t mean that we’re friends in the traditional Webster’s dictionary definition of friends.
Lorelai: Right.
Rory: Friendish might be a better term.

Season two passes in a blur of book talks, music debates, arguments, veiled comments, and finally a car wreck that sends Jess back to New York and leaves Rory in Connecticut with a broken wrist and no goodbye. She ditches school and goes to visit him, missing her mother's business school graduation and realizing that maybe, just maybe, she thinks of Jess as more than a friend. When he returns and finds her at Sookie's wedding she greets him with a kiss.

And then she runs all the way to Washington for a summer leadership program.

When she gets back, she finds Jess' mouth attached to that of a skanky blonde's in the middle of Town Square during the end of summer festival. They end up arguing back and forth until she finally breaks up with her boyfriend at the Dance Marathon and both of them decide to face up to the fact that they want to be together.

And for a while, they're good together.

But when Jess' father comes to Stars Hollow in search of his son, Jess blindly follows him back to the land of everlasting sunshine, leaving Rory without a goodbye (again).

Rory: You know, I have actually thought about this moment. A lot. What would Jess say to me I ever saw him again? I mean, he just took off, no note, no call, nothing, how could he explain that? And then a year goes by. No word, nothing, so he couldn't possibly have a good excuse for that, right? I have imagined hundreds of different scenarios with a hundred different great last parting lines, and I have to tell you that I am actually very curious to see which way this is going to go.
Jess: Could we sit down?
Rory: No. You wanted to talk, so talk. What do you have to say to me?
Jess: I love you.

Nearly a year goes by and not a word. And then, in an unexpected confrontation at (yet another) festival, Jess mutters three other words that she never expected to hear from him. A couple months later, after returning for his mother's wedding, he begs her to come away with him and she says no. (And every Lit fan feels their heart break in unison with Jess').

Jess: I know you. I know you better than anyone! This isn't you.
Rory: I don't know. Jess: What are you doing? Living at your grandparents' place? Being in the DAR? No Yale - why did you drop out of Yale?
Rory: It's complicated!
Jess: It's not! It's not complicated!
Rory: You don't know!
Jess: This isn't you! This! You going out with this jerk, with the Porsche! We made fun of guys like this!

A year and a half goes by before our favorite bad boy returns, this time with a book engraved with his name on the front cover and the town princess residing at her grandparents' mansion due to her decision to drop out of Yale. He's shocked to find Rory behaving like someone else entirely and, out of everybody in her life, he's the one to finally snap her out her stupor and get her back on track.

The last time Jess appears in the series is a heartbreaking moment for all Literati fans. After Logan cheats on her, Rory runs to Philedelphia to visit Jess at the opening of Truncheon, a bookstore/art gallery/performance space that he opened with friends. He thinks their debt to fate has been paid and the timing's finally right for them to be together but, after a brief kiss, Rory's the one to leave him for a final time.