In need of publicity for his new hotel, Chuck decides to move up his clubs opening and enlists Serenas help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chucks approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivias (guest star Hilary Duff) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (guest star Simon Miller). Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.