Back in New York, Dan is all by himself. His little sister is off vacationing in Europe, while his ex-girlfriend is in the Hamptons. Frustrated with his lack of company, Dan gets a job where he befriends a man named Greg. In the Hamptons, Serena and Blair meet their new roommates- Ibiza and Svetlana. They dislike the fact that their roommates are exact replicas of them and are always trying to get them into trouble. Vanessa has her hands full babysitting the twins. The twins are allowed to do whatever they want which gives a great degree of challenge for Vanessa. Nate also his hands busy working on his coach's yard. But Nate has his eye on a girl- one that is not Blair. Will Nate pursue this new girl or will he and Blair reunite?
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