Serena decides to throw Jenny Humphrey an intimate party for her sixteenth birthday, but things get 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 agrees to help Chuck with a scheme to make Blair jealous, while Vanessa sees an opportunity to make Nate jealous at the same time… but she’s plan failed .Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education. Blair reveals some unresolved feelings between her and Nate. Chuck and Vanessa have sex.
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