1x13 - Gilmore Girls

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.