Season 1, Episode 6: “The Handmaiden’s Tale”

Originally aired: October 24, 2007
Writer: Jessica Queller
Director: Norman Buckley

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. Blair is having a masquerade party, where Nate must find her by midnight for them to consummate their love for one another. Vanessa and Jenny sneak into Blair’s party, and Serena gives Jenny some of her outfit - with her face hidden, she can be mistaken for Serena, which Nate does mistake her for, and kisses her, thinking Jenny is Serena. Nate does not find Blair in time. Jenny also manages to get revenge on Chuck, by leaving him half-naked outside of the ball in the cold. After the party, Chuck says “little Jenny Humphrey manages to get me out of my pants and I didn’t even enjoy it.”