On the anniversary of Bart Bass’ death, Chuck wrestles with the dilemma of following his conscience, or that of his father. After Serena decides to leave Tripp, she reverses course and goes back to see him, going on a trip to Nassau County where an event occurs that shatters the calm of the Upper East Side. Jenny meets up with Damien, but this time for her own course.

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Thanksgiving dinner becomes uncomfortable for Serena when Lily invites Trip and his wife to attend. Meanwhile, Blair thinks her mom is keeping a secret from her; Rufus discovers Lily has been lying about Cece; and Vanessa has a fight with her mother.

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Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien (guest star Kevin Zegers), the son of an ambassador who is staying at Chuck’s hotel, but the experience proves to be a lot more intriguing than she expected.

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Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion.

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Olivia says something she regrets during her appearance on Jimmy Fallon’s talkshow and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather will stop at nothing to get Trip elected to congress. In the midst of another feud with Serena, Blair befriends a new “it” girl and takes her to an election night party at Chuck’s hotel, hoping to make Serena jealous.

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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 infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.

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Vanessa, in an attempt to win her mother’s approval, tries to win the honor of giving the freshman toast at NYU but must square off against Blair in order to do so. Meanwhile, Dan invites Olivia to meet Rufus and Lily, which causes problems for the couple. Serena and Nate work together to help Carter.

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Lily and Rufus decide to move up their wedding day, but someone or something may come between them before the day arrives. Chuck learns a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes, as Blair tells Nate about her suspicions about Bree.

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During the first day of school at Constance Billard, Jenny takes her place as the new Queen Bee. However, Blair gets in her way. Lily returns home to find that things are not as they were when she left them with Rufus. At NYU, Olivia Burke, an actress, enrolls and is assigned to be Vanessa’s roommate.

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Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby’s. Serena begins to think that Carter may have returned to his old habits, Georgina becomes interested in Dan, and Vanessa thinks that something is wrong with Scott.

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