Uncle Jack arrives in New York to help Chuck following his father’s death, but must find him first. Blair, trying to forget her fight with Chuck, turns her attention to getting accepted to the Colony Club.

A sudden tragedy strikes the lives of every teen and parent on the Upper East Side.

Chuck and Blair make a bet to choose the perfect date for each other for the annual Snowflake Ball. Lexi has her sights set on Dan leaving Serena confused with her feelings. Nate and Vanessa are forced to be together leaving their emotions and friendship in danger of being burnt.

It’s Thanksgiving time and Blair is offended when her Mom’s new man hijacks her Thanksgiving traditions. Lily attempts to fix Jenny and Rufus’s frail bond. Eric discovers a secret on Bart.

Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for Vanity Fair.

Serena invites Aaron to a charity event, but soon uncovers a secret Aaron has been keeping from her. Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Meanwhile, Jenny and Agnes plan a fashion show.

Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side, and also to confront, Eleanor Waldorf, who is attempting to “borrow” Jenny’s designs. Meanwhile Serena and Dan attend Rufus art opening as friends, but then Serena meets an artist, Aaron Rose, and the evening gets a little uncomfortable. Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.

Vanessa tries to blackmail Blair into being a nicer person, with the pictures of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but Serena do not want to follow the rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

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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.

Fashion Week is here!!! Blair is furious with her mother for giving Serena and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf show. Hurt by both Serena and his mother Blair decides to sabotage the show. Meanwhile, Dan starts hanging out with Chuck, but he quickly learns that the dark side has its risks. Lily learns a secret that her new husband, Bart has been keeping from her.