Julie seeks out an old high school crush and brings him to bed with her and Arthur; Billy finds a father figure in Denise's husband, Nate.

Julie and Billy attempt to capitalize on the success of Hamilton by writing and starring in their own historical musical.

Julie faces a moral dilemma when she gets cast in Woody Allen's new TV show; Billy and Marilyn scam their way through a government gay conversion therapy program. Matthew's ex-wife comes to town.