Season 2, Episode 7

Chuck in Real Life

8.4/ 10October 20, 200842 min

Vanessa uses the scandalous picture of Catherine and Marcus to blackmail Blair into being a nicer person, so Blair seeks revenge by enticing Chuck to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena isn't ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Directed by
Tony Wharmby
Written by
Lenn K. Rosenfeld

Guest stars

All episodes — Season 2

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  1. S2 E1

    Summer Kind of Wonderful

    Sep 1, 20088.241 min

    As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with a married, older woman. Blair returns from abroad with a hot guy on

  2. S2 E2

    Never Been Marcused

    Sep 8, 2008841 min

    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

  3. S2 E3

    The Dark Night

    Sep 15, 20087.941 min

    In a humorous twist, Blair questions the lack of passion in her relationship with Marcus, while at the same time Chuck appears to have lost his "passion" for any woman other than Blair. Meanwhile, Nate struggles between his feelings for Van

  4. S2 E4

    The Ex-Files

    Sep 22, 2008841 min

    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

  5. S2 E5

    The Serena Also Rises

    Sep 29, 2008842 min

    In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, at the suggestion of her protege Jenny, has given Serena and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf show. Hurt once again

  6. S2 E6

    New Haven Can Wait

    Oct 13, 20086.842 min

    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 sch