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Tyra Banks appears as Ursula, an actress co-starring in Olivia's film and someone who Serena befriends when she is hired by Olivia's personal assistant for an upcoming film premiere.Lily and Rufus decide to move up their wedding day.As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all traditional rules of dating as would be expected.Meanwhile, Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen.Feeling left out of the planning, Blair attempts to win Chuck's approval by secretly helping him with a problem concerning the opening night.Meanwhile, Dan is unnerved when he finally watches one of Olivia's infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Roberts (Simon Miller) in one of her films.
As Serena prepares to depart for Brown University, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even.
Chuck discovers a secret that Carter has been keeping from Serena which involves Bree and the Buckleys.
Dan and Vanessa are pulled into one of Georgina's schemes when she lures Scott back to New York on a ruse to break up Lily and Rufus.
Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee of Constance Billiard. Olivia says something she regrets during her appearance on Jimmy Fallon's talk show and tries to keep Dan from finding out.
Elsewhere, Rufus gets Lily into the Halloween spirit by taking her out to a costume party. With election day around the corner, Nate suspects his grandfather will stop at nothing to get his cousin Tripp (Aaron Tveit) elected to congress.