Fran Weston dies and Lorelei and Sookie try to buy the Dragonfly Inn; Rory and Jess try approaching each other but fail to talk; Dean tells Rory that he's engaged to Lindsay; Mrs. Kim agrees to let Lane go to the prom with Dave; Luke finds out about Jess and Dean's fight at the party and gets even angrier at Jess, Jess' father comes to Stars Hollow and Luke tries to scare him out of town before he makes raising Jess even harder for Luke.

Rory finally learns her mother can't afford to buy the Dragonfly Inn since financial aid for Yale didn't come through. She decides to take matters into her own hands with a quick visit to her grandparents right before graduation. Luke has second thoughts about a trip with Nicole after something Lorelai tells him. Jess makes silent contact with Rory after her graduation ceremony from Chilton.