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.

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.

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.

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.

Ray irritates Lenore and risks losing a client by giving Claire marriage advice. Tanya tries to prove she can land a big fish for Ray after being humiliated by Lenore during a meeting with a 60-year-old widow. Ray uses his sex earnings to pay for the school baseball team’s transportation to away games, raising Mike’s suspicions. Jessica embarrasses Darby by crashing an eat-in protest outside a fitness gym. At the end of a long day, Ray reconsiders accepting a gift delivered by his neighbor’s wife, Yael.

Spurred by criticism from Damon and Darby, Ray tries to prove he's not an insensitive ex-jock. Seething from the demands of her new boss at work, Tanya turns to Charlie for advice on how to deal with an even more irritable problem: Lenore. Meanwhile, Jessica feels the pinch of the economic downturn, but can't stomach Ronnie's remedy.

Ray gives Lenore an ultimatum, and probes Tanya about the possibility of cutting ties with her fellow pimp. Disturbed that Damon has defiled the school baseball diamond, Ray considers Tanya's suggestion that his son find a new hobby to shake him out of his recent doldrums. Ignoring Ray's warning, Lenore offers Jessica advice in dealing with Ronnie. On his way to meet a new client, Ray has to think on his feet when he runs into Mike in a hotel lobby.

Ray must choose sides between Yael and a new client; Tanya turns to Charlie for stress relief; Lenore learns of Tanya's duplicity; Liz surprises Ray with a revelation about her personal life.

Ray's unscheduled appointment with Claire threatens his participation in a student-alumni baseball game; Frances has doubts about her affair with Mike and her business relationship with Tanya; Ronnie delivers a stern message to Ray.

Ray considers leaving the business; Tanya is emotionally frayed after encounters with Damon and Vera-Joan; Jessica makes a decision about the future.

Ray, Tanya and Lenore's new partnership starts inauspiciously when Ray "holds back" during a tryst with a pregnant client.

Jessica turns to Ray for help with a rodent problem that may be imaginary. Rebuffed by Ray in her attempts to add Mike to her stable, Tanya gets guilt-management advice from Charlie (Lennie James), then goes to extremes to prove her success. Ray has difficulty thawing a client who is cold as ice.

Mike accuses Ray of betraying him; Ronnie has a big fight with Jessica at the dermatologists' banquet; Tanya gets things off her chest when she goes into confessional mode and tells Ray, Lenore and Horny Patty exactly what she thinks of them.

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.

Tanya finally gets Francis to agree to dinner with Ray and Lenore is continuing to be a pest as usual. Ray can tell that Mike is struggling to not continue with his life and tells that he needs to look at himself and tell himself that he is wonderful. Damon goes back to the Poetry Bar and embarrasses Darby after which he has a performance "enhancing" scone and sees Jessica and Ronnie naked. Ray has to choose whether to cancel on the big client or his son who needs him.

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 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.

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.

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.

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.

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.

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.

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.