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.

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.

Ray and Tanya must convince a bank officer and her friend that their "Wellness Center for Women" idea is financially sound. Lenore discovers a new prospect to rival Ray.

Tanya takes matters into her own hands after Jason steals one of Ray's clients. Lenore discovers some surprising news about Jason. Meanwhile, Jessica tries living on her own, and Charlie asks Tanya for a favor. Ray works with a new client who likes to dress up as a cop.

Ray worries that his cover might be blown when he confuses one of his former students with a client. Tanya finds her self taking care of a convicted felon, and Jess takes a job working the Dr. Matt Kopylov's office, the husband of Ronnie's mistress. Lenore makes a deal with Jason's fiancée, Sandee.

Ray and Tanya conspire to get rid of an explosive client. Charlie advises Tanya to keep Lydia happy. Lenore manages Sandee's rising demands, and Matt and Jessica bond.

After Ray tells Lydia he's leaving the business, she takes Ray and Tanya on a ride they will never forget. Darby threatens to leave home, and Lenore confronts Jason about missing a date with a client.

When his shoebox of cash goes missing, Ray goes after the prime suspect: Lenore. His investigation lands him a brand new client named Kyla. Meanwhile, Sandee offers Tanya the opportunity to expand her business.

Ray’s night with Kyla leaves him wondering who she really is; a competition develops at the Wellness Center; Tanya gets help from Charlie in finding out what happened to Ray’s money.

Tanya discovers that Charlie has skipped bail, and she asks Missy, the mother of Charlie's child, to help locate him. Lenore declares war on Tanya and the Wellness Center, and Sandee tries to position Jason to take Ray's spot. Ray faces concerns about his ability to satisfy women, particularly Jessica.

The guest list for Frances and Mike's wedding doesn't include Tanya; Ray takes back what was his after a physical confrontation with Jason; Tanya finds a connection with Charlie's kids.

The survival of Tanya and Ray's business depends on Charlie's whereabouts; Jessica is accused of negligence by Matt; and Lenore tries to get Sandee out of the picture for good.