Gilmore Girls: Jess’ 5 Best Decisions (& 5 Worst) | Screen Rant
Introduced as Luke's uncontrollable nephew sent from New York, Jess starts his Gilmore Girls journey on everyone's bad side. He does nothing to hide the utter disdain he holds for the cutesy, neighborly town of Stars Hollow and each of its residents.
Jess makes several bad decisions as he struggles to adjust to his new life. However, with the support of Luke and Rory's faith in him, he begins to make better choices. Jess' strength of character continues to develop even after his time as a regular on the show, and he frequently comes back to thank the people who helped him along the way.
Following the physical and emotional wreckage of Jess and Rory's car accident, Jess returns to New York, leaving Rory to attempt to repair her relationship with Dean. Jess' second return to Stars Hollow doesn't end on the best terms, but it is one of the better decisions Jess could have made.
Jess' relationship with Rory and parental influence from Luke help to form him into the person he later becomes. If Jess had stayed in New York, he never would've gotten the chance to fall in love with Rory and learn how it felt to have a stable home life.
One of Jess' best storylines in Gilmore Girls is his journey toward getting his own novel published. While we don't see these events on-screen, Jess' appearances in later seasons reveal that he has begun working for a small publishing group in Philadelphia.
Having struggled to follow the rules and authority in high school, it makes perfect sense that Jess would thrive in a creative environment where he can write and publish what he wants. His decision to join Truncheon Books marks the first big leap in the right direction.
When Jess surprises Rory at her grandparents' house, he's surprised to discover that she has dropped out of Yale and is dating Logan. Refusing to sit and allow Logan to insult him, Jess leaves the bar and confronts Rory's behavior.
Though the conversation outside of the bar may have been harsh, it turns out to be one of the best things Jess could have done for Rory at the time. Jess helped Rory put her life into perspective, eventually leading to her getting back on track with Yale and reconciling with Lorelai.
After being visited by Jimmy, the father who abandoned him as a baby, and flunking out of high school, Jess refuses to follow Luke's rules and instead leaves Stars Hollow to head to sunny California. At his lowest point and unsure of what to do next, Jess tracks down his dad and discovers he has an entire family of his own now.
By confronting his father after 17 years, Jess is able to get closure. Though the relocation was intended to introduce his own spin-off, Jess' time in California allows him to realize the mistakes he's made and see that he's on track to follow in his father's footsteps unless he changes.
While he had to be guilted by Luke into attending in the first place, Jess' return to Stars Hollow for his mother's wedding benefits him in the long run. After Luke's self-help journey gives him the confidence to ask Lorelai on their first date, he gives the book to Jess.
Luke helped Jess see that he deserved better than falling into the same cycle of relationships as his uncle. Both men continually struggle to communicate with their partners which is one of the reasons that Jess and Rory didn't work as a couple.
Most of Jess' choices were immature early on in his character arc, causing many of the problems he faced in Stars Hollow. While gnome-napping Pierpont and stealing 500 baseballs didn't have any lingering negative effects on Jess' standing in town, one decision, in particular, permanently put him on Lorelai's bad side. By holding onto Rory's lost bracelet, Jess put her through an unnecessary panic just to prove a point about her dwindling relationship with Dean. Lorelai's distrust of Jess is cemented when she catches him returning the bracelet to Rory's room and he admits to having it the whole time.
Although being "beaked" by the swan made for a hysterical plotline, it also caused more tension between Jess and Rory when he refused to tell her how he received the black eye. After arriving late to dinner with Rory and Emily, Jess' evasive answers led Rory to believe Jess had been in another fight with Dean.
Instead of telling Rory the embarrassing story, he attempts to politely continue with dinner. Rory forces the issue, however, and Jess becomes defensive, leaving before they even began eating. The lack of communication and trust between the pair continued to create problems long after the swan attack.
Instead of telling Rory that he won't be graduating and therefore can't take her to the Stars Hollow prom, Jess bottles up his anger and joins Rory at Kyle's party. Rory's attempts at cheering him up yield no results and Jess continues to take his frustrations out on her.
When Rory tries to comfort Jess, he pushes her to move faster than she's ready and ignores her repeated requests to slow down. Though Jess instantly realized what he had done and went after Rory to apologize, Dean had already found her, assuming the worst and picking a fight with Jess.
Many of the problems in Rory and Jess' relationship are a result of their lack of communication skills. Jess frequently hides his emotions and Rory never gets the hang of asking for what she wants out of their relationship. Jess fails to realize this until it's already too late, choosing to leave Stars Hollow again without saying goodbye to Rory.
Jess allows Rory to find out from Luke and Lorelai that he left, yet again leaving Rory without any chance for closure. To make matters worse, Jess loses his nerve when calling to congratulate Rory on her graduation and remains quiet on the other end of the line while Rory says goodbye to him.
When Jess finally catches up to Rory after their chaotic chase through the town, he tells her that he loves her and leaves before ever giving her the chance to respond. Jess' fear of rejection is evident from the way he is always prepared to leave people before they get a chance to leave him.
Despite showing immense courage by telling Rory he loves her, Jess is still too fearful of having his heart broken to chance her rejection. If Jess had waited to hear what Rory had to say, the pair may have been able to work through their past trauma and make the relationship work.