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It's the annual snowflake ball in the Upper East Side. For the occasion, Blair and Chuck make a bet that they can find the ideal dates for each other. Aaron's ex-girlfriend, Lexi, expresses an interest in Dan which creates conflicted feelings for Serena. Nate, Jenny and Vanessa get into a tangled situation that puts their friendships and hearts on the line. And somebody gets into an accident.
Thanksgiving in the Waldorf household finds Blair upset that her mom's new boyfriend, Cyrus, has decided to ruin all her favorite traditions, but that's nothing compared to what's coming next. Lily finds herself trying to broker a peace treaty between Rufus and Jenny who is prepared to cut off all communication with her father if she doesn't get her way. Serena isn't quite ready to come clean with Aaron about her complicated past, but Dan ends up accidentally revealing a few tidbits of his own. Blair and Chuck come to their friend's aid when Nate is once again forced to confront his father's abandonment. Finally, Eric discovers a secret that Bart has been keeping from Lily.
Blair is against the idea of her mother, Eleanor, with a new man in her life, named Cyrus Rose, and she in her natural and evil ways, does everything in her power to make it impossible for them to be together. Meanwhile, Jenny and Agnes move in together into their own apartment, against Rufus protest. Serena and Aaron fall for each other, but something about Aaron threatens to ruin their new relationship. Elsewhere, Dan and Chuck are at war due to Dan's true interest in Chuck's father Bart.
Serena invites Aaron to be her guest at a charity gala, but then begins to question whether Aaron is the guy she thought he was.
Meanwhile Blair strives to get into Yale, while Jenny gets ready for the night of her life.
Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends, but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.
Vanessa begins her own slide on a dark path when she tries to blackmail Blair into being a nicer person, with the photos she took of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa to steal her phone camera. Meanwhile, Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but the Serena do not want to follow the rules. Elsewhere, Dan and Jenny discover a big secret that Nate has been keeping from them.
Blair, Serena, Dan, Nate and Chuck go to Yale. After Blair and Serena get into a fight, Serena decides to get even with Blair, who has always dreamed of going to Yale, by going to Yale instead of going to Brown as planned and accepting the Dean of Yales private invitation to the campus. Dan discovers that none of his recommendation letters for Yale were sent, he tries to figure out a way of getting into the school. Also Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.
Eleanor gives Serena and her new socialite friend, Poppy Lifton (Tamara Feldman), front-row seats to her Fashion Week show, and this infuriates Blair. Elsewhere, Dan takes a walk on the wild side and tags along with Chuck.
When Dan starts getting cozy with Amanda, the new girl at school, Serena turns to Blair and her minions to step in to sabotage her chances. Vanessa also enlists Blair's help when she finds out a scandalous secret about Catherine.
Serena (Blake Lively) and Dan (Penn Badgley) are forced to deal with their unspoken problems while trapped in an elevator during a citywide blackout. In a humorous twist, Blair (Leighton Meester) questions the lack of passion in her relationship with Marcus (guest star Patrick Heusinger), while at the same time Chuck (Ed Westwick) appears to have lost his “passion” for any woman other than Blair. Meanwhile, Nate (Chace Crawford) struggles between his feelings for Vanessa (Jessica Szohr) and his more-complicated-by-the-day relationship with Catherine (guest star Madchen Amick). Jenny (Taylor Momsen) risks losing her internship when Eleanor (Margaret Colin) catches Jenny critiquing one of the Eleanor Waldorf designs.
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