Jordan's twin sister, identical in every way except hair color and the addition of fake boobs, is in town. Jordan tells Charlie that the two don't get along ever since her sister slept with her former fiancee. She asks Charlie to help mend the damage between them, but he winds up sleeping with the twin. Elsewhere, Lacey's sister blackmails her into buying her whatever she wants in exchange for not revealing to their parents that the marriage to Patrick is a sham.
Charlie invites a new therapy patient named Bob (Bob Clendenin) into the group, who casually tells everyone that he is the devil. Nolan makes a deal with Bob to sell his soul in exchange for Lacey falling in love with him. When Lacey is all over Nolan at the next session, even the skeptical Charlie starts to wonder. Meanwhile, Jen falls for a new neighbor while Sam falls for a young man who appears to be the neighbor's son, but the two are later revealed to be gay.
Charlie accepts a new patient, a pimp named Ray James II, into his therapy group. After Charlie sleeps with a young woman called Sasha (Anna Hutchison) who approached him at the bar, she reveals that she's a hooker and that Ray sent her as payment for his sessions. Meanwhile, Lacey, Nolan and Ed are creeped out by Ray, and attempt to hold their own self-help session without Charlie present.