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Blair has to decide between meeting Chuck at the Empire State Building or risking their future together. A gossip about Dan causes problems for Serena and Nate. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Meanwhile, Georgina Sparks returns to the Upper East Side with an agenda.

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Things start to get tense between Rufus and Will, and Serena chooses to stand by her father, while Rufus starts to feel like an outsider in his own home. Meanwhile, Jenny deliberatly tells Will something that can destroy Lily and Rufus’ marriage. After many attempts, Chuck makes the ultimate grand gesture to get Blair back, hoping that she realizes that they are destined to be together.

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Serena’s father, Dr. William van der Woodsen, returns to the Upper East Side and ensues conflict with Serena, Lily, and Rufus. Because of Jenny’s recent actions, Serena’s and Jenny’s step-sister bond enxounters an obstacle. Blair finds the college where she belongs when she visits the Colombia campus. Dan discoves another secret that Vanessa has been hiding from him.

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Chuck, wanting his best friend back, plans with Jenny to break Serena and Nate up. Meanwhile, Serena’s father, Dr. William van der Woodsen, returns.

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Chuck offers to throw Dorota’s wedding before Dorota’s parent’s arrive from Poland and see her pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Meanwhile, Serena lies to Nate telling him she’s having breakfast with the Humphreys when in reality she goes to meet with Carter Baizen. Rufus discovers that Lily has been lying to him about where she is.

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Chuck and Blair’s relationship is faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny tries to sabotage her. Meanwhile, Dan and Vanessa’s relationship hits a bump in the road.

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Jack Bass is back in NY and Chuck finds himself at odds with his uncle. Eleanor puts Blair in charge of making sure her fashion show is a huge success with an important client. Rufus tries to get Jenny to be more good by volunteering to help in Eleanor’s fashion show, but it takes a turn for the worse when Jenny finds out that Agnes is one of the models.

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Despite being grounded, Jenny continues to see Damien who pressures her to sleep with him. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s very risky. Meanwhile, Dan and Vanessa explore the new stage of their friendship, while Chuck is forced to make a very difficult desicion about his hotel.

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Rufus and Lily suspect something bad about Jenny’s and Damien’s relationship. Chuck learns more about the woman at the cemetery who may or may not be his mother. Meanwhile, Dan and Vanessa struggle with the awkwardness of dating other people.

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Nate and Serena explore their friendship. Blair thinks Chuck is having problems forgetting the woman he saw at his father’s grave. Jenny go with Damien to a State Dinner but she wasn’t aware that it was also to help him with a drug exchange. Vanessa and Dan try to move past Dan’s confession. Rufus returns from a ski trip and tries to avoid Lily.

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