S02E01: Summer, Kind of Wonderful

The first episode of Season 2 (Monday, September 1 at 8 p.m. ET), “Summer, Kind of Wonderful,” finds the privileged posse of the Upper East Side summering in the swanky Hamptons.

As the summer draws to a close, Serena and Nate (Chace Crawford) have everyone fooled into thinking they’re a couple, to cover up Nate’s rendezvous with an older woman (guest star Madchen Amick, My Own Worst Enemy). Blair returns from abroad with a hot guy on her arm (guest star Patrick Heusinger, The Nanny Diaries), making a very jealous Chuck question his decision to leave Blair stranded at the heliport.

Having spent the summer assisting a famous author (guest star Jay McInerney, Gia), Dan decides to head to the Hamptons to see how things stand with Serena, while Jenny (Taylor Momsen) sneaks an invite to a much-coveted Hamptons White Party and bumps into real-life socialite Tinsley Mortimer.

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