<P> Chuck introduces her to Damien Dalgaard, son of the Belgian ambassador who works as a drug dealer to make his own money . Jenny liking his wild lifestyle, eventually strikes up a relationship with him and aids him in supplying drugs to his customers while sharing in some of the profit, even stealing some of Lily's "headache pills". Eventually Lily and Rufus find out about the drugs, which Damien covers up with a story about his father . Against Rufus's will, Jenny continues her relationship with Damien who seems interested in taking it further . Jenny, who is a virgin, backs out at the last minute causing Damien to break up with her, leaving her to face her family . </P> <P> On Rufus' suggestion, Eleanor reemploys Jenny to help out with her upcoming fashion show . Jenny is happy to be back, but is shocked to learn that one of the models she'll be working with is her old friend Agnes, who, after the show finishes, takes revenge on Jenny by drugging her and leaving her in a bar to be taken advantage of . Jenny is rescued by Nate, however before anything happens to her . Because of this though, Jenny's feeling towards Nate reawakens and she aspires to win him over . She tries to kiss him but he resists her advances because he sees her only as a friend and because he is dating Serena . Jenny attempts to sabotage Serena and Nate's relationship by lying to Serena and implying to Nate that she is having an affair with Carter Baizen . Jenny's attempts fail, and her relationship with both is left tenuous after Nate kicks her out of his apartment . </P> <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, as was recently revealed) 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 informs Chuck via telephone that there is something very wrong about the medication that Serena's father is prescribing her . It is discovered that, William has lied to Lily about her condition and has been giving her drugs that in fact make her sick in a plot to win her back off 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 that the police will be coming to get him, and urges him to escape . Back at the van der Woodsen penthouse she reveals that it was she who warned Dr. van der Woodsen and that she wishes her family can go back to normal stating "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 that 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 a picture of Dan and Serena in bed together to Gossip Girl, jeopardizing Dan and Nate's friendship, Dan and Vanessa's relationship, and breaking up Nate and Serena's relationship . Blair confronts Jenny telling her that "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 . However, afterwards, 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 out high school with her mother in Hudson . </P>

Who does jenny end up with on gossip girl