Jess Mariano is the troubled love-interest of Rory Gilmore, son of Liz Danes,Jimmy Mariano and nephew of Luke Danes. He appears in Stars Hollow in Season 2 after Liz sends him to live with Luke, who is unprepared for caring for a troubled youth. He develops a romantic interest in Rory, and his interest is reciprocated, but Rory is still with her first boyfriend Dean Forester. Jess, however, causes Rory to do a number of unlikely things such as skip school, miss Lorelai's Graduation and cheat on Dean by kissing Jess at Sookie's wedding. Dean eventually gets sick of being the obvious second fiddle and breaks up with Rory at the Dance Marathon after months of speculation by many people over the attraction, for which he is unfairly blamed. Rory and Jess have a tumultuous relationship, with Jess being less committed and reliable than Dean, which is frustrating for Rory. Jess seemed excited about the prospect of Rory attending Yale and continuing their relationship while she's in college, however due to extreme number of absences, he eventually fails school, and leaves Stars Hollow for Venice Beach, California, where his estranged father, Jimmy Mariano lives.
This depature was unexpected, with Jess telling neither Luke nor Rory. He continues to call Rory while in California, never talking, but on her graduation day she tells him that she could have loved him, but wasn't going to pine. Jess disappears for most of Season 4 but returns to the show to retrieve his car that Luke had taken and hid to prevent Jess from leaving town at the end of the previous season. After getting his car repaired, and several run ins with Rory (in which he was always the one to walk away first), Jess finally confronts her before he leaves town again, giving Rory his perfect parting line of "I love you" before turning and walking away, again.
Jess does not appear until the end of the season after Luke forcibly suggests that he come to his mother's wedding to T.J. It is here that Jess reads Luke's self help book and realizes that he has been treating Rory all wrong. He appears at her Yale dorm, and asks her to come away with him. This, however, is at the same time that Rory has been getting closer to her now married ex-boyfriend Dean. Jess tells her not to say no unless she doesn't want to be with him, and she declines. After this rejection, Jess leaves without another word; again. Jess moves to Philadelphia where he joins a small publishing house,and writes a novel. He visits Rory while traveling to Hartford to talk to independent bookstores about carrying his book.
He goes to dinner with Rory and Logan Huntzberger, but leaves after Logan mocks him. He ends up confronting Rory about how she has been spending her life - dropping out of Yale, living at her grandparents' house, and joining the DAR. Their talk inspires Rory to move out of her grandparents' house and resume attending Yale. Several months later, Jess' publishing house has an open house, and he invites both Luke and Rory . Luke attends with April, and Jess meets his cousin for the first time. Rory attends alone, and she and Jess kiss, but Rory confesses that she is in love with Logan and that she came because she was angry that Logan cheated on her. Jess is angry at being used but tells her that she can tell Logan that something happened if it will make her feel better. It is worth noting that Rory cheated on both of her boyfriends, Dean and Logan, with Jess. Jess has difficult relationships with his relatives. Originally resentful of being forced out of New York and to Stars Hollow, he begins to appreciate having a stabilizing influence in his life in Luke, eventually paying him back all the money that he owed and telling Luke how much he appreciates what Luke did for him. He also attends Liz's wedding to TJ and walks his mother down the aisle. Milo Ventimiglia has stated that he was happy with the way that the character was left, and that he didn't need to come back during as hoped by the creators. At the end of the series, Jess is the only one of Rory's ex-boyfriends with whom she is on good terms.