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| They Shoot Humphreys, Don't They? airdate: Nov. 9, 2009 directed by: Alison McLean written by: Amanda Lasher |
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| Not satisfied with just being Queen of Constance Billard, Jenny (Taylor Momsen) sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Nate (Chace Crawford) and Chuck (Ed Westwick) plot to help Serena (Blake Lively) and Blair (Leighton Meester) repair their damaged friendship. Dan (Penn Badgley) is upset when Olivia (guest star Hilary Duff) contemplates leaving school for a movie project. Jessica Szohr, Kelly Rutherford and Matthew Settle also star.
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- Jenny: Your era is over, and so is that headband.
- Blair: Girls like her run emotional Ponzi schemes.
- Serena: But have fun tonight. These are probably the last people in New York who still think you matter.
- Blair: This is not like your wedding day, Cotillion only happens once.
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- Jonathan broke up with Eric
- Serena and married Congressman Trip flirted
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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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