1.06 "The Handmaiden's Tale"

Dan is torn between two girls when his childhood friend, Vanessa, returns home and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate is ultimately still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny and Dan sneak into the ball. Elsewhere, Lily asks Rufus to accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous.