Cleveland takes an offer from his boss, Mr. Waterman, to quit his job with six months of severance pay, but struggles to find a way to tell Donna. Meanwhile, Rallo finds a handsome and charming man (guest star Kid Cudi) for Roberta (Reagan Gomez), after Federline forgets their anniversary, but Rallo is shocked to discover that the new guy is a strict disciplinarian when it comes to kids.