Season synopsis
Contains spoilers for this season and earlier seasons.
Rory and Jess finally date, but his habit of skipping school and disappearing leaves her hurt and frustrated. At the dance marathon, Rory’s attention to Jess helps Dean see that their relationship is over; he later dates Lindsay. Jess works extra shifts to buy a car, falls short of graduating, misses prom, and pressures Rory to have sex before fighting Dean. After a visit from his estranged father, Jess leaves Stars Hollow without telling Rory or Luke. Lorelai, meanwhile, tells Emily and Richard she will not reunite with Christopher and repairs her rift with Luke.
The season also gives Rory’s friends their own turning points. Lane becomes the drummer in a local band and secretly dates guitarist Dave Rygalski, while Mrs. Kim’s approval comes only after Dave pleads for Lane to attend prom with him. Paris and Rory’s friendship strains over school politics and Paris’s relationship, then deepens when Paris turns to Rory after failing to get into Harvard. Richard takes the Gilmore girls to Yale and arranges an interview; Rory realizes she wants Yale, despite having long pictured Harvard, and Lorelai comes to accept her choice.
Richard gives Lorelai money from an investment made when she was born, so she repays her parents for Rory’s school fees; that choice costs Rory financial aid and rekindles Friday dinners when Emily and Richard agree to fund Yale. The Independence Inn is badly damaged by fire and eventually closes, while Lorelai and Sookie revive their plan to buy the Dragonfly Inn and Sookie discovers she is pregnant. Rory graduates as Chilton’s valedictorian, thanks her grandparents and Lorelai in her speech, and prepares for Yale as she and Lorelai leave the school together.