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Also, Blair is suspicious of Bree and shares her concerns with Nate.
Sonic Youth performs "Starpower" at the wedding reception.
Unfortunately, Georgina turns up as Blair's roommate in the dorms, determined to make Blair a social outcast.
As Serena prepares to depart for Brown University, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even.
Elsewhere, Serena and Nate team up to help Carter win money at a poker table to free him from his arrangement with the Buckleys.
In need of publicity for the opening of his new Empire Hotel, Chuck decides to move up the hotel's nightclub opening and enlists Serena's help to get the word out to her celebrity clients.
Georgina takes an interest in Dan, and Vanessa begins to suspect that something is not quite right with Scott.
Bree's true intentions with Nate are secretly revealed—having something to do with Carter and his gambling habit.
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An Upper East Side face-off ensues when Blair and Chuck both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high.
Meanwhile, Serena suspects that Carter may be up to his old habits with gambling and being not completely honest with her.
Vanessa, hoping to finally win her difficult activist mother Gabriela's (guest star Gina Torres) approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU.
Meanwhile, Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple.