Ray seeks guidance to help him with his problems and his first task is to find a winning tool for financial success. Tanya, also attending the self-help group, helps Ray.

Tanya enlists the help of a former colleague Lenore to help Ray in exchange for names and numbers of rich women.

Howard Koontz a nosy neighbor of Rays's accuses him of public indecency. While Damon and Darby want their father. Ray and Tanya struggle with their partnership until a plan reignites their dreams.

The students of Lakefield vote for Coach ray as their recipient for the fundraiser bur Ray finds it embarrassing. Tanya has other ideas to boost Ray's career as a gigolo. Damon is left reeling when his sister rejecting his help.

An unhappy, beautiful, new client (Gemma) requests a "do over" for a role-playing fantasy -- which makes Ray feel like a frustrated dancing monkey. But he is eager to succeed because he promised a car for Damon and Darby, to capitalize on Jessica's new economic situation. Tanya agrees to go on a date with Floyd with ego-crushing results.

Tanya takes offense with Jemma for skipping over her to directly set up Ray's "dates." Still mad for having her dog put down, Jessica confronts Ronnie about their finances, learning that times may not be as bad as he makes them out to be. After Jemma asks Ray to open up about himself, he gives his basketball team an inspiring pep talk.

Ray and Jemma's professional relationship becomes clouded as they begin falling for each other. Meanwhile, Tanya receives unexpected help in easing her writer's block. Ray is invited for a family dinner by Jessica. And Ray "scratches" his neighbor's beautiful back so that she can return the favor.

Ray asks Tanya for relationship advice; Tanya receives some unsolicited marketing tips from Lenore; and Ray finds himself in an awkward place while at a barbecue given by Jessica and Ronnie.

After a satisfied client expresses no intent of reacquiring Ray's services, Tanya is disappointed and later begins to pitch their business to her co-workers. Damon hangs out after school with his bisexual friend in detention. Ray chances upon Lenore at the mall and receives lessons in branding.

Tanya becomes worried that Lenore may try to control Ray, who is unnerved by a possibility of layoffs at the school. Meanwhile, Jessica searches for a way to end a marital rut, and Damon bonds with Darby over a souring relationship.