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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 naívely 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.