Lorelai chauffeurs Rory to Sherry's baby shower in Boston and finds herself dragged into the festivities against her will; Miss Patty gets a new beau; Jess comes home with a car and Luke tries to find out where he got the money to pay for it; one of Stars Hollow's more eccentric citizens requests a permit to mount a demonstration in the town square.

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.

Rory and Paris have lunch at Yale with Richard, who introduces them to his friend, Professor Asher Fleming; during Friday night dinner at the Gilmore residence, Lorelai asks for an invitation to the Yale-Harvard game even though Rory clearly gives her an out; Emily is irritated when Lorelai shows up for the game wearing Harvard colors; the Gilmores tailgate in style with flasks, an RV, a BBQ, and servants to wait on their guests; Emily is upset when Pennilyn Lott, Richard's first girlfriend, shows up and asks about the Inn, and Richard is forced to confess that he has continued to have a semi-annual dinner with Pennilyn the entire time that he and Emily have been married; Lorelai takes Jason up on his earlier offer of a dinner date, but they end up leaving the stuffy restaurant and having a great time dining al fresco at a local grocery store; Rory walks back to the dorm after the game and discovers Paris kissing Asher Fleming.

Lane sneaks out of the house when Gil gets the band a 1:00 a.m. gig at CBGB's; Luke and Lorelai take matters into their own hands when newly restored church bells turn out to be less welcome than originally anticipated; Rory gets personal with William during a political discussion when she suspects that he's been spreading embarassing stories about her; Lorelai is initially distressed when she learns that Luke has moved to Litchfield to live with Nicole, but a visit to his apartment over the diner dispells her worries; Lane and her mother have a long-overdue talk with life-changing consequences after Mrs. Kim discovers her daughter's secret life.

Wanting to make peace with Rory, Christopher shows up at Yale, but she brushes off his attempt at compromise. When Lorelai learns that Christopher's father dies, she spends the evening at his place trying to comfort him, then disdains to tell Luke the truth about where she was. Also, Emily & Richard are briefly reconciled when they find and take in a lost dog.

After months of separation, Sookie tries to reconcile Rory and Lorelai by asking them to be the godmothers of her two children. However, they both end up fighting when Lorelai realizes that Rory didn't see fit to share her new cell phone number with her.

Logan comes home from the hospital and is cared for by an overprotective Rory; Liz has big news for Luke; Emily has LASIK eye surgery, so Lorelai has to serve as her chauffeur; Rory is upset by a statement Logan's dad made about her in an interview in the Wall Street Journal; Jackson discovers that former employees planted marijuana in one of his fields, and he and Sookie try to dispose of it.