<P> At a gala event where Serena's recently returned father William Van Der Woodsen is making a speech, a former client of Damien's approaches Jenny, angrily telling her the drugs she sold her (Lily's cancer medication) gave her a yeast infection . Rufus overhears this and grounds Jenny to the Humphrey apartment in Brooklyn . During her punishment, Jenny researches Lily's medicine and tells Chuck there is something very wrong with the medication Serena's father is prescribing her . It is discovered that William has lied to Lily about her condition and been giving her drugs that make her sick in a plot to win her back from Rufus . Seeing an opportunity to break up Rufus and Lily and return her family to the way it was before, Jenny attempts to sabotage Blair, Chuck, and Nate's plan to unveil William's deception . When William is about to be held accountable, she quickly runs to William and warns him, telling him the police are coming to get him, and urges him to escape . Back at the van der Woodsen penthouse she reveals that she warned William and says she wishes her family could go back to normal: "When I lived in Brooklyn, I may have had to ride the subway to school, and make my own clothes, but at least our family was happy". Rufus says the only thing that needs to return to normal is Jenny . Eric is hurt by Jenny's attempt to leave the family, and says that if she wants out, no one is forcing her to stay . </P> <P> Jenny hits rock bottom after sending Gossip Girl a picture of Dan and Serena in bed together, jeopardizing Dan and Nate's friendship, Dan and Vanessa's relationship, and breaking up Nate and Serena's relationship . Blair confronts Jenny, telling her, "Nate loves Serena, Dan loves Vanessa--God knows why--and Chuck loves me . But you, Jenny? No one loves you except your daddy . And after what you pulled yesterday, who knows if that's even true anymore?" Emotionally distressed, Jenny goes to Nate's apartment but instead finds Chuck devastated over his break - up with Blair and in her state of vulnerability, Jenny loses her virginity to Chuck . Afterward, Blair arrives willing to take Chuck back and Jenny sneaks out . She breaks down in tears to Eric, telling him that everyone hates her and that she slept with Chuck . Eric tells Dan, who confronts Chuck just as he is about to propose to Blair . Jenny, in tears, leaves with Rufus and Lily . A week later, she says her goodbyes to her family and leaves to finish high school with her mother in Hudson . </P> <P> Jenny has been living in Hudson with her mother since May . Blair finds Jenny preparing for an interview with Tim Gunn, and grants her a special day pass . When Chuck steals Jenny's portfolio, she is forced to visit The Empire Hotel, where Blair had forbidden her to go . This results in Blair and Jenny scheming against each other, and Jenny eventually telling Gossip Girl that she lost her virginity to Chuck, not Damien Dalgaard . While Jenny is left feeling victorious, a defeated Blair blames Chuck . Jenny ultimately realises the damage of her return and decides to leave for good, telling Blair and Chuck that their vindictive games against each other will soon destroy them both . </P> <P> Juliet and Vanessa Skype Jenny, asking for help to take down Serena . Jenny doesn't want to go back to her old tricks but also feels Serena is to blame for everything that happened last year and can never take blame for anything, so she agrees to help with the scheme . But when Serena ends up in the hospital after being drugged by Juliet, Jenny tells Juliet that she is going to come clean with everyone about their scheme . Juliet warns her that she will be going down alone . When Jenny appears at the hospital, Vanessa has already pinned the entire scheme on her; unable to defend herself, she leaves, showing up at Blair's later that night, telling her that Juliet was behind everything and that she and Vanessa were merely accomplices . To prove her story, she hands Blair Juliet's masquerade mask and earns Blair's forgiveness . After confessing to Blair, she says she would love to help her take down Juliet, but she should return to Hudson rather than become involved in another scheme . </P>

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