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Dan (Penn Badgley) makes elaborate plans to impress Serena (Blake Lively) on their first official date. The same night, Jenny (Taylor Momsen) is invited to the infamous Blair Waldorf (Leighton Meester) sleepover and finds herself in a high stakes game of "truth or dare."

Meanwhile, when Lily (Kelly Rutherford) discovers that Eric (Connor Paolo) is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus (Matthew Settle). Chace Crawford and Ed Westwick also star.

The episode directed by Jamie Babbit was written by Lenn K. Rosenfeld.

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