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| 303: THE LOST BOY airdate: 9/28/3009 directed by: Jean DeSegonzac written by:Robert Hull
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| | It's an Upper East Side face-off when Blair (Leighton Meester) and Chuck (Ed Westwick) both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high. Serena (Blake Lively) suspects that Carter (guest star Sebastian Stan) may be up to his old habits, Georgina (Michelle Trachtenberg) takes an interest in Dan (Penn Badgley), and Vanessa (Jessica Szohr) begins to suspect that something isn't quite right with Scott (guest star Chris Riggi). Chace Crawford, Taylor Momsen and Matthew Settle also star. | |
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- Dan: "I wanted to talk to you about us, not not us us, it's uh, look here's the thing, I really love hanging out with you but I just want to make sure that there’s not a misunderstanding, that we’re on the same page about us, uh, hanging out like we do. If you want me to leave I can understand. "
- Serena: "Who doesn’t have a Georgina in their closet?"
- Bree: "Go ahead and run if you want, you know how much Daddy loves to hunt."
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- Serena and Carter broke up and then got back together.
- Vanessa's man Scott moved back to Boston.
- Dan cools things off with Georgina.
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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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| | SONG TITLE |
| ORIGINAL ARTIST | | Animal |
| Miike Snow | | Ready for the Floor |
| Lissy Trullie | | Weld at the Seams |
| The Broken Remotes | | Check the Score |
| The World Record |
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- What is Georgina going to do once she gets to Boston?
- What did Carter do to Bree's family?
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| It's the first day of school at Constance Billard which means it's also time for Jenny to take her rightful place as the new Queen Bee. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that she may be needed back at Constance. Meanwhile, Lily returns home to Rufus and her family to find that things are definitely not as she left them. Plus, a famous movie actress, Olivia Burke (recurring guest star HILARY DUFF - A Cinderella Story, Material Girls, Lizzie McGuire), enrolls at NYU in hopes of having a somewhat normal college experience, and is assigned to be Vanessa's roommate. Guest star TYRA BANKS (The Tyra Show, America's Next Top Model) appears as Ursula, an actress co-starring in Olivia's movie and someone who Serena befriends.
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