Lorelai, Sookie, Emily, Michel, and Rory go to a drag club for Lorelai's bachelorette party; Emily regales the group with stories about the week before her wedding, some of which give Lorelai pause about her own feelings about marriage; when everyone else leaves to call their sweeties, Lorelai calls Christopher instead of Max; later that evening at home, Lorelai announces to Rory that she's calling the wedding off because she's realized that Max isn't the one for her; mother and daughter decide to take a road trip to avoid the sympathies of all of Stars Hollow.

Rory embarks upon a campaign to improve Lorelai's relationship with Jess, and convinces her to let him clean out their gutters so he can make some extra money.

Luke can't stand how cramped his living quarters have become now that his sister has sent all of Jess's things to Stars Hollow, so he goes apartment hunting, first with Jess and then with Lorelai, who finally finds him a great place to live. When he finds out later that Taylor will be his new landlord, he explodes, tells Taylor to throw out his application, impulsively buys the building which houses his diner and the flower shop next door, and begins to take down the adjoining wall to expand his living space.

When Dean notices that Rory isn't wearing the bracelet he made for her, she covers her shock at its loss and lies that she removed it because of a rash on her arm. She searches for it frantically all over Stars Hollow, not realizing that Jess picked it up after she dropped it on the bridge two weeks earlier when they shared

Rory's application for Harvard arrives, plunging Rory, Lorelai and Emily into a frenzy; a Chilton seminar on college applications only adds to Rory's anxiety and sends Paris into a tizzy; Taylor steamrolls Luke into opening a soda shop next to the diner; Lane places an ad in the paper for a band and finds a musical soulmate; Lorelai and Rory have dinner with a Harvard alumni and his family which may assure her chances of acceptance; Dean has a talk with Rory about their future after she goes to Harvard.

Luke and Nicole have a successful first date; Jess and Dean trade verbal blows; Sherry goes into labor with only Lorelai and Rory for company; Lorelai reminisces about her pregnancy and Rory's birth; Lorelai introduces Emily to modern entertainment technology; Richard and Emily decry Lorelai's and Rory's plans to backpack through Europe; the war between Paris and Rory continues when Paris picks a photo of the ""Franklin"" staff for the yearbook that has the worst possible shot of Rory.

Emily and Richard rejoice when Rory announces her decision to attend Yale; Kirk sustains baking-related injuries when Rory secretly enlists the help of her fellow Stars Hollows citizens to bake the world's largest pizza for her mother's birthday party; Michel and Tobin compete over giving Lorelai the best present, but Richard wins the contest hands-down with a check for $75,000 that's actually the proceeds from an investment he made in Lorelai's name at her birth; Luke confronts Jess about skipping school to work at Wal-Mart, but is blown off as usual; when Lorelai decides to use the money to pay back her parents for Rory's Chilton tuition, Emily becomes furious with Richard for giving Lorelai the money, fearing that the repayment of their loan is a sign that she'll never see either Lorelai or Rory again; Luke makes a bad impression on Nicole's parents, scaring them off with a rant on the horrors of parenting Jess.