Gossip Girl (2007)

S1E6 The Handmaiden's Tale

Dan is caught in a love triangle when his childhood friend Vanessa comes back to New York, professing her feelings for him just as he and Serena are navigating their own relationship. At the masked ball, Blair sets up a scavenger hunt for Nate, but he can’t shake his feelings for Serena. Despite Blair's rule about no outsiders at the event, Jenny and Dan manage to sneak into the ball in disguise. Meanwhile, Lily invites Rufus to join her at an Eleanor Waldorf event with the intention of making Bart Bass envious.