On their first free Friday night, Lorelai and Rory are at a loss over how to spend the evening, while Emily and Richard cavort at the party they're hosting; Lorelai is appointed Grad Night Treasurer and runs into a playing-it-cool Max at her first Chilton Booster Club meeting; Lane's band gets their first gig at a party and rocks the house, but Dave rocks Lane's world when he flips out after discovering that Young Chui is in love with her; a despondent Lane indulges in a little too much beer, and then drunkenly calls her mother and confesses all; when staff cutbacks at the Inn force Lorelai to do turn-down service, she becomes very unsettled at seeing a cozy Luke and Nicole in the room she's offered as thanks for Luke's help with repairs after the fire; Jess's inability to tell Rory that his frequent absences have caused him to flunk out of school and miss graduation and the prom prompts an argument between Jess and Rory, and then a full-blown brawl with Dean after Dean comes upon a te

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; Jess's father comes to Stars Hollow.

Back home for the weekend, Rory has an uncomfortable encounter with Dean, her ex, and ends up getting invited to his wedding the next day. Meanwhile, Lorelai and Sookie visit Michel at his trendy new workplace, but run into problems getting the permit they need to begin construction on the inn.

The demands of the electorate are beginning to get to Jackson; Lorelai and Rory delicately nudge Richard and Emily closer together; Lorelai decides that a double date with Rory and Dean is the way to smooth over the bumps in her relationship with Dean, but the evening goes awry when Luke can't get over feeling that Dean isn't good enough for Rory; Richard takes up a new hobby, and Emily buys a panic room; failing to get a response from Zack about the declaration of her feelings, Lane rescinds them, which finally gets Zack talking; Lorelai introduces Luke to ""Pippi Longstocking"" as Kirk gets much better acquainted with Lulu during movie night at the Black & White & Read Bookstore.

Old man Twickum dies, declaring through his will that the house be made into a museum for two months, then disposed of by the Head of the Historical Society, aka Taylor. Much to everyone's surprise, Luke volunteers to help with the museum to remain close to the house; Lorelai is interviewed by a magazine due to her success with the inn; Lane suspects Zach of cheating on her with Sophie; Rory and Paris sulk over their recent pitfalls with love, resulting with the both of them in Stars Hollow, getting tipsy with Lane on Miss Patty's Punch, and all three of them trying to contact their beaus; Dean informs Luke that their situations are the same, and that Lorelai will eventually get bored and move on; Lane discovers Zach secretly practicing in a Bluegrass band.