The new "evolved" Charlie has to deal with a ghost from his old carousing, baseball-playing days when a unattractive woman he slept with just to break a batting slump shows up as a new patient in group therapy.

Charlie and his ex, Jennifer, are having an issue with how Charlie still tries to manage her life when Cleo - one of Charlie's patients from his prison anger therapy group - shows up on his doorstep, fresh out on parole. Jennifer decides to get back at Charlie by dating the ex-con.

Charlie goes too far when he gets jealous of Jennifer's much younger boyfriend, Canvas. Meanwhile, Patrick helps Lacey look sexy for her first modeling gig.

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.