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Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Blair sets out on a mission to break up her mother and Cyrus Rose, her new man.
Jenny moves in with Agnes as the two continue with their plans for their own fashion line.
Jenny befriends a young model, Agnes, who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf, who is attempting to "borrow" Jenny's designs.
Blair is over the moon that she is dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love, Marcus, when he introduces Blair to Marcus' stepmother who happens to be Catherine.
Meanwhile, Nate learns the downside to having an affair with Catherine when he keeps getting caught in his lies and learns his family has gone bankrupt due to his father jumping bail.
After Blair and Serena get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale, by ditching her plans to visit Brown, and instead accepting the Dean of Yale's personal invitation to visit the school.
After discovering that none of his recommendation letters for Yale were ever submitted, Dan frantically tries to figure out a way to salvage his chances of getting into the school.
Dan has spent the summer assisting a famous author.
While interning for Eleanor Waldorf's company, Jenny sneaks an invite to a much-coveted Hamptons' White Party at which Eric introduces her to socialite Tinsley Mortimer.
Blair and her minions decide to befriend the new girl, Amanda, in order to sabotage her possible new relationship with Dan.
Vanessa discovers a scandalous secret about Catherine and enlists Blair's scheming expertise to use the information to help Nate.
As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.Tags: Adult Dating, affair dating, sex dating