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.