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| HOW TO SUCCEED IN BASSNESS airdate: Oct. 26, 2009 directed by: Joe Lazarov written by: Sara Goodman |
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| In need of publicity for his new hotel, Chuck (Ed Westwick) decides to move up his club's opening and enlists Serena's (Blake Lively) help to get the word out to her celebrity clients. Feeling left out of the planning, Blair (Leighton Meester) attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Dan (Penn Badgley) is unnerved when he finally watches one of Olivia's (guest star Hilary Huff) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (guest star Simon Miller). Jenny (Taylor Momsen) is forced to choose between her relationship with Eric (Connor Paolo) and her new role as Queen Bee. Rufus (Matthew Settle) gets Lily (Kelly Rutherford) into the Halloween spirit. Chace Crawford also stars.
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- Blair: "Tell those pathetic trick or treaters that there is no prepackaged joy for them here."
- Jonathan: "Hello Invasion of the Body Snatchers. Looks like Jenny, sounds like Jenny, is really a dark power-hungry monster."
- Eric: "Rufus asked my size this morning, does that mean I am getting a flannel?"
- Dorota: "It's hard to love a powerful man."
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- Chuck and Blair make up.
- Dan and Olivia are going strong.
- Serena is fake dating Patrick, a movie star.
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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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