Serena (Blake Lively) decides to throw Jenny (Taylor Momsen) an intimate party for her sixteenth birthday, but things get way out of control when Poppy Lifton (guest star Tamara Feldman) turns the small gathering into a huge social event. In a moment of weakness, Vanessa (Jessica Szohr) agrees to help Chuck (Ed Westwick) with a scheme having to do with Blair (Leighton Meester) and Nate (Chace Crawford). Rufus (Matthew Settle) learns that Dan (Penn Badgley) will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education.