Welcome to New York's Upper East side where the wealthy and connected mingle at benefits and try to deal with their always dramatic love lives, not to mention picking colleges. Blair Waldorf is the so-called toast of adolescence in her world; she and her friends, Kati Farkas and Isabel Coates, go to a prep school and fancy parties with their rich parents. Blair is envied by her adversaries because she is thought to have the perfect life, not just because of her gorgeous boyfriend, Nate Archibald, but because she's also planning on getting into her dream college,Yale. With everyone worried about college(or procrastinating on worrying, which everyone seems to be doing), and senior year dragging along, her seemingly perfect life is interrupted by her ex-best friend, the beautiful Serena van der Woodsen, coming back into town after getting kicked out of boarding school. Serena comes back into her life, and into the eyes of Blair's boy friend. When everything Blair knows starts to fall apart, everyone will realize that her life is far from perfect. Will life in the the Upper East Side redeem itself of what it's really supposed to be? Or will the false facade reveal that the rich have the same problems as the not so rich (Jenny and Dan Humphrey), if not more. And just maybe Jenny and Dan are all the more happy with their simple, not so expectant lives
The annual Cotillion Ball is about to take place. Blair is not going with Nate, but she finds herself being featured in The New York Times and is enjoying her secret affair with Chuck. Serena is not going, so her grandmother, CeCe, shows up to change her mind. Jenny volunteers for the ball and Lily takes her under her wing. But the night of The Cotillion is the night of Alison's first art opening, and Rufus and Alison say Jenny cannot attend the ball. Jenny decides to defy them both. Refreshed by Blair's newly buoyant attitude, Nate asks her to The Cotillion and she says yes, which makes Chuck jealous. CeCe tells Lily and Serena that she is sick and her last dying wish is to see Serena go to the ball, and she wants Serena to go with Carter Baizen. CeCe insults Dan and offers to pay Rufus off to convince Dan not to go with Serena. Dan learns of this and tells Serena that he does not think very highly of CeCe, which results in a huge fight between them. Serena decides to go to the ball with Carter. Chuck manipulates Nate into thinking Carter is having an affair with Blair, so Nate punches Carter at the ball.
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