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.

Blaire 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, but 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 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 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.

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.