First aired: 9/1/2008
Summer in the Hamptons!! In the second season premiere, our favourite Upper East Siders endure the Summer heat in the Hamptons. During the trip in the Hamptons, Blair meets a charming new boy hoping to make Chuck jealous, Nate gets involved in a steamy relationship and Serena questions her past relationship with Dan. Meanwhile on the other side of town, Dan gets a job at a local library. Though things don't go according to plan.
Writer: Joshua Safran
Director: J. Miller Tobin
Guest star: Matthew Settle (Rufus Humphrey), Tinsley Mortimer (Herself), Patrick Heusinger (Marcus), Mädchen Amick (Catherine), Jay McInerney (Himself), Michelle Hurd (Laurel)