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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
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.
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 her 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.
Blair and her 'Posse' interview different girls to decide whether or not they would be inducted into their 'clique'. Dan bumps into new student Amanda and they form an instant bond however, Blair and her 'posse' attempt to sabotage Dan and Amanda's friendship by inducting her as the new girl in their 'clique' meanwhile, Serena meets a new lust interest and Vanessa meets with the Duchess.
Serena and Dan are trapped in an elevator during a citywide blackout making them work out their differences. Marcus and Blair have problems of their own which is passion. While Chuck has problems in having no passion with women other than Blair. Nate struggles with his feelings for Vanessa and Catherine.
The identity of Lord Marcus\' mother is revealed - which leaves our favorite Upper East Siders shocked. Nate and Serena get closer. Chuck and Lord Marcus begin an unexpected friendship and Blair makes a revelation.
Summer in the Hamptons!! In the second season premiere, our favourite Upper East Siders endure the Summer heat in the Hamptons. During the trip in the Hamptons, Blair meets a charming new boy hoping to make Chuck jealous, Nate gets involved in a steamy relationship and Serena questions her past relationship with Dan. Meanwhile on the other side of town, Dan gets a job at a local library. Though things don't go according to plan.
Blair takes matters into her own hands to help Serena with the manipulative and evil Georgina Sparks. Lily, while keeping Rufus in her mind, prepares for her wedding with Bart Bass that is designed to be the Upper East Side's social event of the year. Serena finally tells Dan the whole truth about her past and they try to work things out after Dan has cheated on her, will it be too late? An unexpected guest shows up at Lily and Bart's wedding. Georgina goes somewhere where she can do no harm. Blair plans to go somewhere with Chuck.
Serena slips back into her old habits because she is ashamed of her secret. She eventually reveals it and her friends Blair, Nate and Chuck have to put their differences aside, in order to help her. Unfortunately, Serena is too ashamed to share the truth with Dan, therefore he assumes the worse about his girlfriend. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night.
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