When Jimmy's old girlfriend Stacey has dinner with Beth and Jimmy, Beth is shocked to learn that her husband had proposed to Stacey several years before. Jimmy's troubles worsen when it is revealed that he gave the same ring to both women. Later, as Jimmy attempts to redeem himself, hip-hop star Marques Houston, a guest on Jimmy and Carl's radio show, offers Jimmy some advice: Propose to Beth again and give her a new diamond ring.

Carl's sister Chloe, a video producer, comes to town and convinces Beth and Jimmy to let Otis audition for a part in her new music video, but when they discover the role calls for a baby girl, the sight of seeing his son in a dress rehashes a painful, gender confusing memory from Jimmy's own childhood. Meanwhile, Chloe and Carl are in ""Ike and Tina"" mode from the start, battling it out on the radio and internet with Chloe revealing childhood secrets to his audience that Carl would rather have left forgotten.