Ray Drecker is a struggling high school coach in Detroit who is descending to all-time lows in his professional and personal life. He attends a self-help group in a desperate attempt to find a plan for financial success. Tanya, an old flame, is also attending the self-help group and she gives Ray inspiration in an unexpected way.

Ray's life continues to frustrate: His neighbor Koontz is on his case for urinating in the lake; he and Jessica continue to argue over the best way to parent the twins; and it turns out Lenore has disappeared, along with his wallet.

The students of Lakefield vote for Coach Drecker as their recipient for the fundraiser but Ray finds it embarrassing. Tanya has other ideas to boost Ray's career as a gigolo.

A client who is unhappy wants to revisit a role-playing fantasy; Ray promises a car for Damon and Darby, to capitalize on Jessica's frugality. Reluctantly, Tanya agrees to go on a date with Floyd.

Ray starts to fall for Jemma, which clouds their professional relationship. Tanya receives unexpected help for her writer's block. Jessica invites Ray to a family dinner.