Juliet Annastasia Sharp

Juliet Sharp is a student at Columbia University and the main antagonist of the first half of Season 4.

Personolaty
She had a personal vendetta against Serena van der Woodsen because she believed she was the reason her brother is in prison although it was later revealed that it was actually Lily who did it.

Season 4
She has a brother, Ben Donovan, in prison who is the reason why the both of them have a vendetta against Serena. Her cousin, Colin Forrester, is a professor at Columbia whom Serena had a relationship with, before finding out he was her teacher. She apparently comes from a not-so wealthy family and has to live on financial support for her rent and book fees. She has a manipulative agenda and seems to be awfully good at twisting words and persuading others in her battle to bring Serena down. She often guilt trips to make them do things that further her scheme. When exposed she covers up all her lies and convinces most people of her innocence with deceitful tales. Through the first ten episodes of season 4 she constantly plotted against Serena and after recruiting Jenny and Vanessa she successfully destroys her relationship, albiet only temporarily, in the Saints and Sinners party and got her admitted to the Ostroff Center by faking her overdose. In the eleventh episode her history is finally revealed: She came from a humble family from Connecticut and her older half-brother Ben Donovan who taught as an English teacher at the same boarding school that Serena attended before the beginning of the series. He and Serena grew close, as she valued him as someone who took her seriously without attempts at exploiting her. They shared a mutual affection for each other, and while Serena attempted at spending the night with him, he declined her due to their teacher student relationship. Later, he is charged with having a sexual relationship with Serena who was a minor at the time, and was told that she signed an affidavit saying that he did so. In order to keep this scandal out of the papers, he is offered a plea bargain which states that he will spend five years in prison. After confronting Serena about it she realises that her mother was the one who charged Ben and not Serena. They both confront her and she confess she did it so Serena's record from Nighly was erased and could go back to Constance. Realising she was mistaken Juliet apoligises to everyone and left promising not to cause any more trouble. She wasn't seen after that. It is mentioned that she went to do independent study abroad.

Relationships
Serena van der Woodsen (enemy)