Dan (Penn Badgley) is torn between two girls when his childhood friend, Vanessa (Jessica Szohr), returns home and declares her feelings for him, just as he and Serena (Blake Lively) are trying to figure out what they mean to each other. At the infamous masked ball, Blair (Leighton Meester) sends Nate (Chace Crawford) 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 (Taylor Momsen) and Dan sneak into the ball.

Finally, Lily (Kelly Rutherford) asks Rufus (Matthew Settle) to accompany her to an Eleanor Waldorf (Margaret Colin) event in order to make Bart Bass (Robert John Burke) jealous. "America's Next Top Model" winner CariDee English makes a cameo as Bart Bass' date.