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Jess Mariano, played by Milo Ventimiglia, was a main character in seasons 2 and 3, and recurring afterward. He first appears in the episode "Nick & Nora, Sid & Nancy". He combines bad boy traits (rebellious and resentful of authority) with geek traits, being intellectually inclined and well-read. He also shows an interest and ability in magic tricks. He grew up with his mother Liz Danes (Kathleen Wilhoite); his father, Jimmy Mariano (Rob Estes), departed after his birth. Liz sent Jess away to Stars Hollow, Connecticut to live with her brother, Luke Danes because she couldn't handle him and thought that Luke could. But Jess's arrival in Stars Hollow isn't well received by the town at large. Luke has an even bigger problem controlling Jess's personal life at Stars Hollow. Despite his actions, Jess's knowledge of books and pop culture eventually appeal to Rory Gilmore. They become friends despite others' disapproval, and Jess pursues Rory, despite her relationship with Dean. Jess leaves town for a while following a car accident which leaves Rory injured. Rory skips school to visit him in New York, where they officially say goodbye. In the season two finale, he returns for a surprise visit during Sookie's wedding. Rory impetuously kisses Jess, and then begs him not to say anything.
Jess and Rory officially start dating after the local dance marathon when Dean tells Rory he knows she is interested in Jess and breaks up with her. Their relationship runs into trouble because of both Jess's and Rory's constant insecurities and difficulties communicating. Rory later confesses to her friend Lane Kim that, while she was initially attracted to Jess due to their similar interests, she was ultimately too used to Dean's affection and reliability, expecting Jess to treat her the same, only to realize that he never would. When Luke finds out that Jess would not be allowed to graduate from Stars Hollow High because he had cut too many classes, he tells Jess that he must repeat his senior year or leave. Unwilling to accept Luke's stipulations, Jess rides a bus to Venice Beach, California to find his estranged father. He has a brief encounter with Rory on the bus, but she is unaware of his departure at the time. In California, Jess stays with his father.
The WB was originally going to continue Jess's storyline in a spin-off called "Windward Circle". In this new show, Jess works on building his relationship with his estranged father and befriends a bunch of California skateboarders. The Gilmore Girls episode 3.21 "Here Comes the Son" acted as a backdoor pilot for the show. It was originally picked up as a mid-season show, set for January 2004. However, the network cancelled the show before it aired, citing high production costs to shoot on location in Venice Beach as the reason.[1]
Jess briefly returns to Stars Hollow in season four 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 giving her the cold shoulder. 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.
A year later, a much more mature Jess returns to deliver a copy of the book he has written to Rory, 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 teenagers. 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 very possessive of Rory and aggressive toward Jess. Jess politely endures Logan's taunts for as long as possible before walking out (showing that he has matured, as before he would simply have attacked Logan). Although Rory goes after him, Jess refuses to stay. He is shocked that Rory is dating someone like Logan, and more importantly that she has dropped out of school with no plans for the future, 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.
Jess appeared for the final time in the Season 6 episode "The Real Paul Anka", where he, Luke and Rory meet again at the new book store/art gallery/publishing house in Philadelphia where Jess works. Rory and Jess exchange a kiss, but Rory tells Jess that she is still in love with Logan and only did it 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, if it will make her feel better. As of the end of the series, Jess is the only one of Rory's ex-boyfriends with whom she is on good terms.
The Gilmore Girls creaters hint that Rory and Jess get back together after the series ending, as they were on good terms, and they state 'the only one for Rory would be Jess Mariano.'
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