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| 308: THE GRANDFATHER: PART II airdate: Nov. 2, 2009 directed by: Mark Piznarski written by: Lenn Rosenfeld
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| Olivia (guest star Hilary Duff) says something she regrets during her appearance on Jimmy Fallon's (Fallon playing himself) talkshow and tries to keep Dan (Penn Badgley) from finding out. With election day around the corner, Nate (Chace Crawford) suspects his grandfather (guest star James Naughton) will stop at nothing to get Trip (guest star Aaron Tveit) elected to congress. In the midst of another feud with Serena (Blake Lively), Blair (Leighton Meester) befriends a new "it" girl and takes her to an election night party at Chuck's (Ed Westwick) hotel, hoping to make Serena jealous. Taylor Momsen, Jessica Szohr, Kelly Rutherford and Matthew Settle also star.
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- Chuck: " Look ladies, this is supposed to be a classy event, not a sample sale at the outlet mall. "
- Dan: Listen, as much as I enjoy my current girlfriend talking to my ex-girlfriend about her fake boyfriend who is also my current girlfriend’s ex-boyfriend…"
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- Serena breaks up with her fake-boyfriend Patrick
- Dan and Olivia: going strong
- Chair is perfect
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| WTF did they say? Gossip Girl "isms" overheard in this episode:
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ACTOR as CHARACTER |

ACTOR as CHARACTER |

ACTOR as CHARACTER | |
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| Gossip Girl cast |
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