This episode originally aired on October 30, 2001 on The WB
This episode ushers in a new character who will become central to Rory’s life: Jess, the brooding nephew of Luke. With sharp wit, a rebellious streak, and a love for literature, Jess immediately adds a dynamic twist to the Stars Hollow scene.
The episode begins with Luke scrambling to transform his diner and apartment into a welcoming space for Jess, who is being sent to live with him by his frustrated mother. Luke, while apprehensive about this new responsibility, is determined to provide a stable environment for the teenager.
However, Jess’s arrival isn’t smooth sailing. His rebellious nature causes immediate clashes with both Luke and the tight-knit Stars Hollow community. He’s quick to dismiss the town’s quirks and isn’t keen on following rules.
Rory’s first encounter with Jess is both surprising and challenging. When she discovers him going through her personal belongings, including her books, an unexpected connection sparks. Their shared love for literature sets the foundation for a complex relationship.
Lorelai, on the other hand, is trying to navigate the aftermath of her canceled wedding. The town’s gossip, combined with her own feelings of guilt and confusion, make it a tough time. However, it’s her protective nature that shines when she catches wind of Rory’s interactions with the “bad boy” Jess.
Additionally, Lorelai deals with the arrival of Emily in Stars Hollow, leading to comedic situations as Emily tries to fit into the town’s unconventional lifestyle.
Memorable quotes from the episode: