Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side, and also to confront, Eleanor Waldorf, who is attempting to “borrow” Jenny’s designs. Meanwhile Serena and Dan attend Rufus art opening as friends, but then Serena meets an artist, Aaron Rose, and the evening gets a little uncomfortable. Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.

Vanessa tries to blackmail Blair into being a nicer person, with the pictures of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but Serena do not want to follow the rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Blair, Serena, Dan, Nate and Chuck go to Yale. After Blair and Serena get into a fight, Serena decides to get even with Blair, who has always dreamed of going to Yale, by going to Yale instead of going to Brown as planned and accepting the Dean of Yales private invitation to the campus. Dan discovers that none of his recommendation letters for Yale were sent, he tries to figure out a way of getting into the school. Also Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.