Lorelai organizes the Stars Hollow Charity Rummage Sale and buys a sweatshirt donated by Luke. When she wears it into the diner, he goes ballistic, much to her shock. Sookie tells her later that the sweatshirt belonged to his old girlfriend Rachel, who broke his heart. When Lorelai's curiosity gets the better of her and she demands details from Sookie, Sookie teases her about being jealous of Rachel, which Lorelai denies a little too strongly. Lorelai returns the sweatshirt to Luke, reminding him that it's okay to hold onto some good memories.

To the delight of Lorelai and Rory, Sookie gets great tickets to a Bangles concert in New York City. When Lane's mother won't let her join them, Lorelai suggests that Rory invite Paris, Madeline, and Louise, who have gathered at the house to prepare for a school debate. The girls accept and take Sookie's good seats while she and Lorelai head for seats in the nosebleed section that they bought at the door. During the concert, Madeline and Louise meet some cute guys and leave with them to go to a party, over Rory's objections. Lorelai is freaked when she finds out, but finally manages to track them down with the help of Sookie, Rory and Paris.