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Rufus and Lily grow suspect of Jenny’s relationship with Damien. Chuck learns more about the woman who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people.
Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman ) he saw at his father’s grave. Jenny agrees to accompany Damien (guest star Kevin Zegers) to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa and Dan attempt to move past the awkwardness of Dan’s confession of love. Rufus returns from a ski trip and tries his best to avoid Lily
A year after his father's death, Chuck deals with an issue from the past, and another car accident occurs on the Upper East side. Meanwhile, Dan and Vanessa face the new complexities in their friendship; and Jenny gets accused of assaulting a classmate
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
Trying to impress NYU theater kids, Blair uses her contacts to get a private concert with today's hottest performer, Lady Gaga. Dan and Olivia sign up to write and star in an NYU play, based on an idea by Blair and directed by Vanessa. Meanwhile, Serena turns to Nate for help in a dificult situation, now that Blair is not there. As a favor to Chuck, Jenny agrees to hang out with Damien, an ambassador's son staying in Chuck's hotel, and the experience turned out to be more intriguing than what she thought.
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.
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.
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.
Vanessa hopes to impress her mother (Gina Torres) by delivering NYU's freshman toast, but she has to compete with Blair to win this honor. Meanwhile, Dan introduces Olivia to Lily and Rufus, and Serena and Nate join forces to help out Carter.
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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