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.
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