In Gilmore Girls season 4 episode 22, titled “Raincoats and Recipes,” Rory and Dean sleep together. This episode marks a significant moment in their relationship, as Rory loses her virginity to her first love, a few years after they had broken up. Earlier in season 4, Dean marries Lindsay and gets a job with a Stars Hollow construction crew (ironically working on the Dragonfly Inn). Throughout season 4, Rory and Dean reconnect and have a friendship, and it’s soon clear that there’s something more between them.