Rory and Jess experienced an almost instant connection; Rory was the first and only person in Stars Hollow that Jess spoke to with interest and Rory, at first just being nice to him, got interested after his love of books, intellect, humor and charm showed itself.
Jess and Rory meet each other at a very uproarious time in Jess's life. He is unhappy with and disorientated at having been unceremoniously sent to live in Stars Hollow by his irresponsible mother. Once Lorelai invites him into her home to a welcome feast, Jess meets Rory and his interest seems peaked, although he throws a lot of attitude her way all the same. Even realising Rory isn't really like him, emotionally, he still attempts to talk with her when seeing her in town, in spite of his disastrous conversation with her mother. Rory isn't fazed by Jess's attitude, but rather sees beyond the exterior when realising Jess is an avid reader.
The two spar naturally, Jess lends Rory a lot of his books and they eventually start hanging out, though only circumstantially, indicating that it is more than friendship. Jess's discomfort with his life sees him acting out with pranks on the town, and Rory is the only one he listens to/allows to change his mind, which for instance leads Jess to help out Luke. They become friends despite others' disapproval, and Jess pursues Rory, despite her relationship with Dean. Rory is much less direct in her actions, unwilling to face her instant attraction to and strong feelings for Jess, which leads her to continually, unapologetically flirt with him, while staying in a relationship with Dean. After the car accident, Rory begins subconsciously taking charge of those feelings, going to see Jess in New York, forgoing her mother's graduation and, upon his return to Stars Hollow, initiating their first kiss.
Jess is always direct, no bull with people around him as he grew up with an evasive mother and is no less so with Rory, which both attracts her and pushes her to grow if she wants a relationship with him. When Rory returns from Washington, Jess does not relent on this characteristic and has no time for running after Rory, who has not contacted him at all for three months following their kiss. Rory is full of attitude over the fact that she has to confront Jess about his new girlfriend, and he lets her know how insensitive she's been. Rory is furious at this, chiefly as her yen for keeping the status quo as much as possible in her life (ie. staying with Dean) is solely what keeps her from breaking up with Dean.
Rory continues her romance with Dean, despite that her attraction to Jess has been obvious to Dean for months at this point. Repressing her feelings makes her behave increasingly irrationally, especially towards Jess's fling, Shane, whom Rory accosts at the former's work, and throwing deviled eggs at Jess's car. Jess, conversely, is annoyed with Rory dragging her feet, but does come to her aid, but also engages in their frustration-fueled sparring. Finally Rory's tiredness at the dance marathon lifts this thin veil and she openly throws daggers at Jess, until Dean ends their relationship for her.
Jess and Rory officially start dating the day after Dean ends their relationship, and very quickly the subject of sex comes up with Rory, who talks to Lorelai about her feelings, while Luke tries to lay down the law of über abstinence to Jess. Rory and Jess are happy to finally be together, and at first are only bothered by the looming shadow of Dean, whom Rory doesn't wish to hurt any further. Dean threatens to beat up Jess and strikes up a friendship with Rory as a ploy to win her back, which Rory is oblivious to. Jess's insecurities about the people in his life, and himself, causes him to feel uncertain about Dean's presence in Rory's life.
Rory correspondingly tries to assure Jess, but is quick to assume the worst of him and even admits without cushioning it that she trusts Dean, but not Jess, which Jess is very hurt by. This creates a rift in their relationship as Jess, in turn, does not confide his failing high school, nor of his arrangement with Luke that he can only stay in Stars Hollow if he graduates. Pained by his situation, he becomes increasingly sad, but does not confide in Rory who is trying to comfort him. This leads to him lashing out at her and their worst fight exacerbated by Dean trying to punch Jess. The next day his estranged father, whom he has never met, shows up at Luke's Diner and Luke throws out Jess. This is the last drop for Jess who leaves town, and Rory, without telling her. Luke tells Lorelai, who informs the heartbroken Rory (although Rory does not show this to the world). Their ending comes when Jess repeatedly tries to call Rory on her graduation day
Jess briefly returns to Stars Hollow the following year to steal back his car from Luke after his mom tells him Luke stole it from him nearly a year earlier. Jess also sees Rory several times, though every encounter ends with him leaving not to bother her. Jess leaves after telling her that he loves her. A few months later, Jess returns to Stars Hollow for his mother Liz's wedding. After the wedding, Jess visits Rory at Yale and asks her to run away with him. She declines because she says she no longer wants to be with him by saying "No' repetitively.
Two years later, a much more together Jess returns to give Rory a copy of a novel he has written, explaining his new life working at an independent publishing company, and explaining that he could not have achieved any of his recent success had she not believed in him when they were younger. At the time, Rory had dropped out of Yale and moved into her grandparents' house. They decide to get something to eat, but are interrupted by an agitated Logan, who invites himself along.
During the reunion, Logan is incredibly rude to Jess, condescending and arrogant which makes Jess walk out and Rory goes after him, telling Logan not to follow her. Jess is shocked that Rory is dating someone like Logan, and more importantly that she has dropped out of school which Jess knows her to love, and repeatedly demands to know what's going on, telling her "this isn't you, Rory, you know it isn't." His criticism and refusal to accept excuses make Rory take a serious look at her life and are instrumental in her return to Yale.
He then says this is a bad time for them to meet up, so he'll see her another time. Rory and Jess see each other for the last time when she goes to Philadelphia for the open house at Truncheon Books, the book store/art gallery/publishing house where Jess works. Rory and Jess exchange a kiss, but Rory tells Jess that she is still in love with Logan and only kissed him because she found out Logan had been with someone else while they were broken up. Jess is hurt at being used, but says that she can tell Logan something happened. After that he is never mentioned again.
- XTC – Then She Appeared
- First kiss
- Ash – Girl From Mars
- 'Goodnight, Dodger'
- Yoko Ono – O'Oh
- Rory in New York with Jess
- Why Jess Shouldn't Be Team Rory
- MTV september 2016
- Team Jess
- – BUZZFEED february 2016
- Jess Mariano Was Rory's Most Empowering Boyfriend On 'Gilmore Girls', Hands Down
- – BUSTLE february 2016
- Why Jess Was Truly The Most Important Of Rory's Boyfriends In 'Gilmore Girls'
- – BUSTLE february 2016
Margin notes and references
- ↑ 1.0 1.1 Nick & Nora/Sid & Nancy
- ↑ 2.0 2.1 2.2 The Ins and Outs of Inns
- ↑ A-Tisket, A-Tasket
- ↑ Dead Uncles and Vegetables
- ↑ Lost and Found
- ↑ Haunted Leg
- ↑ Lorelai's Graduation Day
- ↑ Back in the Saddle Again
- ↑ Eight O'Clock at the Oasis
- ↑ They Shoot Gilmores, Don't They?
- ↑ Let the Games Begin
- ↑ A Deep-Fried Korean Thanksgiving
- ↑ That'll Do, Pig
- ↑ Swan Song
- ↑ Keg! Max!
- ↑ Say Goodnight, Gracie
- ↑ Those Are Strings, Pinocchio
- ↑ A Family Matter
- ↑ Nag Hammadi Is Where They Found the Gnostic Gospels
- ↑ Last Week Fights, This Week Tights
- ↑ Let Me Hear Your Balalaikas Ringing Out
- ↑ The Real Paul Anka