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.
Guest Stars:
Gregg Henry, Steve Hytner, Loren Lester, Marylouise Burke, John Johns
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.
Guest Stars:
Rebecca Creskoff, Gregg Henry, Gina Hecht, Stefan Umstead, Bach Hoang
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.
Guest Stars:
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.
Guest Stars:
Rebecca Creskoff, Steve Hytner, Alanna Ubach, Margo Martindale, Michael Blaiklock
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.
Guest Stars:
Natalie Zea, Gina Hecht, Steve Hytner, Marylouise Burke, Rhea Perlman
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.
Guest Stars:
Natalie Zea, Steve Hytner, Alanna Ubach, Rhea Perlman, Joshua Leonard
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.
Guest Stars:
Rebecca Creskoff, Natalie Zea, Marylouise Burke, Joshua Leonard, Lauren Weedman
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.
Guest Stars:
Rebecca Creskoff, Steve Hytner, Loren Lester, Marylouise Burke, Alanna Ubach
Guest Stars:
Gregg Henry, Natalie Zea, Marylouise Burke, Grant Harvey, Michael Petersen
Rebecca Creskoff, Gregg Henry, Joshua Leonard, Lauren Weedman, Darlene Hunt