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.