In need of publicity for his new hotel, Chuck decides to move up his club's opening and enlists Serena's help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivia's (recurring guest star HILARY DUFF) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (recurring guest star SIMON MILLER - Elah and the Moon). Jenny is forced to choose between her relationship with Eric (recurring guest star CONNOR PAOLO) and her new role as Queen Bee. Plus, Rufus gets Lily into the Halloween spirit. Musician ALBERT HAMMOND JR. (The Strokes) performs.