- “Paris – Typical guy response. Worship Kerouac and Bukowski, God forbid you’d pick up anything by Jane Austen
Jess – Hey, I’ve read Jane Austen
Paris – You have?
Jess – Yeah, and I think she would’ve liked Bukowski”
- —Jess, Rory and Paris hanging out[src]
Jess is the troubled love-interest of Rory Gilmore, son of Liz Danes and Jimmy Mariano, and nephew of Luke Danes. Jess is incredibly smart, quick-witted, and interested in the arts, but not academically motivated. His lack of parental support from his mother and the absence of his father leaves Jess feeling very alone and scared of the world, which causes him to test or lash out at most people. Jess tends to distance himself from people, leading to his breakup with Rory. Despite people reaching out to him, he often pushes them away without explanation.
Jess comes to Stars Hollow when his mother, Liz, is frustrated with his attitude and bad behavior so she sends him to live with her brother, Luke Danes. Early on, Luke states that in order for Jess to live with him, he must attend school and graduate. Jess also works part-time in the diner his uncle owns. From the start, he and Luke share a very complicated relationship as Luke can't relate to his nephew, and he has no experience with caring for a youth, especially one who is troubled.
However, after staying at Luke's for a while, it is evident that the two care for each other even if it isn't directly stated. Jess quickly develops a romantic interest in Rory Gilmore after he meets her at a welcome to town dinner at her and her mother's house. When they meet, Rory is involved with Dean Forester, a local boy she has been dating for two years. Although Rory never says it out loud, she feels like she and Jess are kindred spirits, sharing very similar interests.
Jess shows his interest in Rory in several situations, but after a tutoring sessions ends in a car accident with Rory in the hospital, Luke puts Jess on the bus back to his mother. Rory unusually skips school for the day and unexpectedly misses her mother's graduation to take a trip to New York to see him, and when he asks her why she came, she says he never said goodbye. Because of this, Jess later returns to Stars Hollow with the intention of doing better than the first time he was there. He finds Rory outside of Sookie's wedding, and she surprises him with a kiss (as Rory is still with Dean). When he kisses her back, she pulls away and starts freaking out resulting in her running away screaming "welcome home"
When Rory is in Washington D.C. for the summer, Jess gets involved with another girl named Shane. Rory returns, and Jess expresses his anger over her still being with Dean and not communicating with him while she was away, especially after kissing him months earlier. Rory stays with Dean after resolving that being with him is the better choice, but she continues to show her attraction and interest in Jess. Jess attends the 24 Hour Dance Marathon with his new girl, and after Rory demonstrates clear jealously over him, Dean breaks up with her publicly at the school dance as he's tired of being dragged along when the two clearly have feelings for each other. Jess finds Rory sitting on the deck at the lake afterwards, and she confesses that everything Dean said about them was right.
Jess eventually agrees that he was right, and they begin their relationship. Their relationship, however anticipated by each other, is bumpy. Unlike Dean, Jess is terrible at communication and follow-through, and this causes frustration for Rory. Also, Jess is jealous of the formed friendship between Rory and Dean, and it doesn't help that Lorelai still doesn't warm to him. Jess arrives late to a dinner at Rory's grandmother's house where he shows up with a black-eye and later walks out on the evening after he and Rory get into an argument.He later reveals he was attacked by a swan and takes luke to the pond to retaliate with a ladle. He also continues to keep secrets from her, like how many hours he's really working at Walmart instead of attending school.
When Rory is accepted to Yale University, Jess seems excited about the close proximity so they can continue their relationship even with her being at school. Rory would like to attend her senior prom at Stars Hollow High with Jess, but when he tries to get tickets, the principals officially informs him that he will not be graduating (and therefore cannot buy tickets). Earlier in the season, Jess had taken a job at Walmart, and he continuously missed school to work extra hours. The principal tells him he would have to repeat the year. Jess keeps this news from Rory, and they attend a party together even though Jess is in a sour mood. Later in the evening, Rory finds Jess sulking in a bedroom upstairs, and she tries to talk to him. Instead, Jess attempts to get intimate with her, but Rory isn't ready for that step.
Jess gets angry and yells at her for bothering him. When she walks downstairs crying, Dean sees her and initiates a fight with Jess. This causes the tension between Jess and Rory to skyrocket, and he walks away from the party without looking back. When Luke finds out that Jess refuses to repeat his senior year, he and Jess get into an argument. Jess declares he won't go back to school, and Luke tells him that since he broke their agreement, he needs to leave. Jess and Rory share an awkward conversation on the morning bus, and when Rory gets off, Jess pulls a book from his duffle bag.
In the next episode, Jess is in Venice, California to see his father (who had surprisingly visited Stars Hollow a few weeks before) and asks to stay with him. His father eventually agrees, and Jess stays in California. This departure was unexpected with Jess telling neither Luke nor Rory. He continues to call Rory while in California, but never speaks when she answers even though she suspects it's him. When he calls again on her high school graduation day, she tells him that she could have loved him, but she wasn't going to pine. She was going to Europe for the summer, and then she was going to Yale. She was going to move on, and she then hangs up because he doesn't speak a single word the whole time.
Jess returns six months later to retrieve his car, which Luke had taken and hid to prevent Jess from jeopardizing graduating from high school. The car is in need of repairs and so Jess stays in town for another day before he can leave. Accidentally, he has several run-ins with Rory, but each time quickly leaves without really allowing her to talk. Right before he is going to leave town with his car fixed, he finds Rory on the streets and tells her that he loves her. However, he once again leaves before letting her respond.
After Luke vehemently asks that he come to his mother's wedding to T.J., Jess settles on coming to Stars Hollow in the spring and walks his mother down the aisle, their relationship with her possibly improving. While in Stars Hollow, Jess reads Luke's self help book and realizes that he has been treating Rory the wrong way all along. 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. Jess leaves.
Jess moves to Philadelphia where he joins a small publishing house and writes a novel. He visits Rory, who is at the time living with her grandparents, to tell her about his book. He gives her a copy to keep, and he tells her it was through her influence that got him to this point. They agree to do dinner the next night. He goes to dinner with Rory and Logan Huntzberger (who comes home earlier than expected), but leaves after Logan mocks him. Outside the restaurant, Jess confronts Rory about how she has been spending her life - dropping out of Yale, living at her grandparents' house, and joining the DAR. He knows this is all very much unlike her because he knows her better than anyone. Their talk inspires Rory to move out of her grandparents' house and resume attending Yale (which then rekindles her relationship with her mother).
Several months later in The Real Paul Anka, Jess's publishing house has an open house, and he invites both Luke and Rory. Luke attends with April Nardini, and Jess meets his cousin for the first time. Jess and Luke share a moment where Jess thanks his uncle for everything and pays him back the money he owed him. Rory attends alone, and she and Jess kiss after the open house concludes. Rory confesses that she is in love with Logan and that she came because she was angry 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.
- Ventimiglia based much of Jess on one of his childhood best friends.
- Liz tells Luke that she thinks Jess is a lot like their father, William Danes.
- Jess has difficult relationship with his family members, but by the conclusion of his appearance, he is on good terms with them.
- Jess didn't graduate from Stars Hollow High. It is not stated if he ever went for his GED.
- Jess buys a run-of-the-mill car from Gypsy. Rory and Lorelai smash deviled eggs on it, and Luke steals it to prevent Jess from working at Walmart.
- Jess was awarded Employee of the Month at Walmart for being their "Mr. Reliable."
- When Jess first came to Stars Hollow, he notoriously did pranks around town (stealing the school baseballs, stealing Babette's gnome, and drawing a chalk outline of a body on the sidewalk).
- Why Jess Shouldn't Be Team Rory
- MTV september 2016