Serena decides to throw Jenny an intimate party for her 16th birthday, but things get out of control when Serena's friend Poppy Lifton, returns and turns the small gathering at the van der Woodsen apartment into a huge social event. Meanwhile, Vanessa agrees to help Chuck with a scheme that will make Blair and Nate jealous... and they end up having have sex in the process. Also, Rufus learns that Dan and he will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education, in which Lily offers to help. Elsewhere, Dan receives a letter from Boston from Rufus and Lily's illegitimate son wanting to meet with him.