Vanessa and succeeds in gaslighting her into toying with Dan and Nate's feelings, attempting to take a foundation position from Blair, and returning to her old partying habits. Serena is rehabilitated while Dan and Blair subsequently discover Juliet's reasons for ruining Serena. Serena was supposedly in an illicit, but not ever consummated, relationship with Juliet's half-brother and Serena's boarding school English teacher, Ben Donovan (David Call) and was arrested when Lily forged an affidavit that falsely accused Ben of statutory rape, out of concern for Serena. The holidays have Serena trying to figure out how to release Ben from prison and her relationship with Lily is yet again strained. Serena and Dan put a possible return to their relationship on hold, knowing that they might not have the same chance of loving and trusting each other. Meanwhile, Ben's release from prison reignites Serena's feelings for him and they pursue a loving, yet troubled relationship. Serena's relationship with Ben slowly erodes when she receives news from Vanessa that he is responsible for hurting Nate's father in prison and when Ben's mother, Cynthia, raises Ben's personal troubles while at the same time seeking to exonerate him. Serena becomes proud of her mother when Lily decides to face the consequences of sending an innocent Ben to prison. Serena and Ben's relationship eventually ends due to family complications. Serena's cousin, Charlie Rhodes, comes to stay with Serena's family for a while. Charlie helps Serena find out that Dan and Blair have had a secret romance, causing a fight between Serena and Blair. Serena continues to use Charlie as a spy until noticing that Charlie is starting to act exactly as Serena and steals Serena's dress. In the season finale, Serena gets Charlie to help with a medical condition, though it is later revealed that Charlie is really Ivy, and Ivy is just acting. Later, while walking the streets of Los Angeles, Serena gets offered a job in Hollywood where she decides to move to. Season 5 In Season 5, Serena is working as a film producer's assistant in Los Angeles and spending her free time with Nate and Chuck. Although Serena's boss, Marshall, is difficult to please, his boss, Jane, promotes Serena after she succeeds at a task that Marshall failed. Later, she runs into Charlie and convinces her to move with her back to New York. When Dan tells Serena, Nate, Blair, Chuck,