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She soon ends up in New York and launches her own online journals: I told her I wanted to send her back in time to screw Racquel Darrian's brains out with a strap-on. Sherri Saum portrays Holland Kemble in season three. She is first introduced in the first season as the new Headmistress and immediately faces trouble with the junior class. Contribute Help us build our profile of Taylor Lautner! Her and Nate's families are rivals and they begin a "Romeo and Juliet" kind of relationship. Taylor lily dating

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  1. In the second season, Carter resurfaces in New York with the mysterious Elle but ends up being involved with Blair and sleeps with her, contributing to her downward spiral. Jenny steals her mother's Valentino dress during Jenny's birthday. She also continues to be Blair's loyal right-hand woman, and the ring-leader of her sidekicks.

  2. She has a short affair with Nate. After her return, Lola inadvertently reveals to everyone that Diana is Chuck's biological mother. She is first introduced in the first season as the new Headmistress and immediately faces trouble with the junior class.

  3. She tells Russell she wants nothing to do with him, but later helps Blair and Chuck when it's discovered that he was responsible for killing her mother.

  4. She first meets Nate Archibald in Los Angeles at a party at her home while Nate claims the house is his and end up in bed together. They did not find them but they have found the ambassador. During the first season, she and Kati often appeared in Blair's Audrey Hepburn dreamscapes and at one point she and Kati also appear in Dan's dreams.

  5. We later learn that he is in fact her cousin, and that the cheque was to cover her rent and school fees, he has no idea of her and her brother's plans for Serena. She is also a national Merit Scholar. He and Juliet devised a plot to destroy Serena's life permanently, however with no real intent on hurting her physically.

  6. He has a relationship with Blair. At the start of season 4, she runs off again, leaving Dan with their son Milo but it is later revealed that he is not the father and that it was just another one of Georgina's schemes.

  7. He begins dating Jenny and wanted to have sex with her, and when she refused he left her. Juliet proceeds to blackmail Lily for a monthly cheque by telling that she will reveal one of Serena's other dirty secrets if she does not provide her with cash. Dan and Nate, thinking that Eric is in the embassy with Damien, went for him.

  8. Moreover, he and Lily also shared a sexual past, although she states that it was a very long time ago.

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