Tanya enlists the help of a former colleague Lenore, who is now a professional shopper, so Ray can offer his services to her clientele of rich older women.

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.

Tanya objects to the break in protocol after Jemma bypasses her to set up "dates" directly with Ray. Jessica confronts Ronnie about their finances, but he refuses to give her a straight answer. After Jemma prods Ray to open up about himself, he gives his basketball team an inspiring pep talk.

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.

After standing him up, Jemma tells Ray they should take a break, and Ray seeks out Tanya for advice on women. Ray finds himself in an uncomfortable situation at Jessica and Ronnie's family barbeque.

Tanya pitches Happiness Consultants to other women in her office, with mixed results. Damon goes to detention to hang out with his androgynous friend, leaving Ray baffled. Lenore gives Ray some lessons in branding and, after a chance encounter at a department store, offers Jessica some lifestyle advice.

Tanya worries that Lenore may stage a coup for control of Ray, who is unnerved by rumors of layoffs at his school.