6. The Handmaiden's Tale

Dan is torn between two girls as an old childhood friend, Vanessa, returns to town with a confession as Serena and Dan figure out what they mean to each other. At the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate makes a shocking confession to a disguised Jenny who uses it as ammunition against Blair. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous. Note: This is Jessica Szohr 's first appearance as Vanessa Abrams. Title reference: The 1985 book The Handmaid's Tale.