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In the reading of Bart’s will, Chuck, Bart’s brother, Jack and Lily learn that Chuck is now the CEO of Bass Industries. Chuck agrees that Jack became his guardian.

Rufus and Lily’s relationship is strained as Rufus searches for details about the child he never knew he had. Noticing the strange way his father has been acting lately, Dan does some investigating and uncovers Rufus and Lily’s secret, and he has to decide now what to do and who to tell the shocking revelation.

Because Chuck is MIA since his father’s funeral, his Uncle Jack arrives on the Upper East Side to find and help him. Trying to forget her last conversation with Chuck, Blair focuses on being accepted into the most prestigious ladies club in the city, Colony Club. Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight.

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 strengthen the frail bond between Rufus and Jenny. Eric discovers a secret about Bart. Vanessa and Chuck help Nate deal with his father.

Blair is against the idea of her mother with Cyrus Rose, a new man in her life, and does everything in her power to make it impossible for them to be together. Jenny and Agnes move in together. Serena and Aaron fall for each other but something about Aaron threatens to ruin their new relationship. Dan and Chuck are at war due to Dan’s true interest in his father Bart Bass.

Serena invites Aaron to be her guest at a charity gala honoring Lily and Bart, but after discovering a secret that Aaron has been keeping from her, she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor. Unfortunately, the teenager proves to be more than a handful, and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into the college of her dreams. Meanwhile, Jenny and Agnes plan a guerilla fashion show that will either launch Jenny’s star or ruin her chances of ever being accepted by the industry.

Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side and to confront Eleanor Waldorf, who is exploiting Jenny by stealing her designs with false promises to help launch her design career. Meanwhile, Serena and Dan attend Rufus’ art opening as friends, but when Serena meets a cute artist, the evening takes an awkward turn. 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 does not want to follow the rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

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 Yale’s 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.