Years ago in high school, Ray Drecker (Thomas Jane) was athletic, popular, and destined for success. Now, as a high-school teacher and bascketball coach, he's underpaid, uninsured, and embittered that his wife of 20 years (Anne Heche) has left him for her dermatologist. After a fire damages the rundown Detroit home he inherited from his parents, Ray's fortunes reach an all-time low when his twin children, who had been living with him, move in with their mom and her clean-freak hubby. Lonely, run-down and at wit's end, Ray attend a local self-help class whose mantra is to identify a pesonal "winning tool" to market for financial successs. After a not-so-fulfilling encounter with a fellow attendee - an ex-flame and would-be poet named Tanya (Jane Adams) - Ray has a "eureka" moment. With the help of Tanya, Ray resolves to take advantage of his greatest asset, in hopes of changing his fortunes in a big way.
Tanya asks her former colleague with wealthy connection for help in getting Ray's business going. Damon and Darby warn their father about Jessica's behavior and begs him to get the house fixed up, but discovers it will cost much more than he anticipated.
A serious rift has formed between Ray and Tanya, as the fallout continues over his first job with Lenore. A new front is opened up in a feud between Ray and his neighbor.
Ray's physical and emotional well being may keep him from going to work, despite that Tanya has lined up a pair of clients. Meanwhile, Damon vows to defend the honor of Darby during a spat with an old ex-boyfriend.
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.
Tanya keeps trying to find clients, and asks Ray to consider lowering his price. Lenore tries to get Ray to work with her.
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.
Ray's new co-partnership with Tanya and Lenore gets off to a rocky start when he "holds back" during a tryst with Claire, a client, so he turns to Tanya for advice. Later, Ray and other teachers picket the school in anticipation of summer layoffs. Jessica, already filled with doubts about her marriage to Ronnie and refusing to take calls from Lenore after her experience with the no-show gigolo, is stung by criticism from Darby and Damon. Looking to get an edge on Lenore and regain Ray's trust, Tanya ventures into a tough neighborhood for liberating pimping advice from a real pro.
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.
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.
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.
When Tanya finds Lenore's sweater in Ray's bathroom, she goes to Charlie for some "relief" and Lenore finds out that Francis is no longer her client and vows revenge. Meanwhile, Ray is caught in the middle and needs to chose between Yael and a new Arab client, Samara. Things get a little complicated and it spirals for the twist.
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.
Mike accuses Ray of betrayal; Ronnie vents his frustrations with Jessica at a dermatology banquet; Tanya lashes out at Ray, Lenore and Horny Patty.
Ray considers leaving the business; Tanya is emotionally frayed after encounters with Damon and Vera-Joan; Jessica makes a decision about the future.
In the third-season premiere, Ray and Tanya get creative to find financing when they hatch an idea to relaunch a proven product. Meanwhile, Lenore stumbles upon a valuable resource that may catch her former business partners off guard.
Ray meets his new rival after he sweeps one of his regulars off her feet, but Tanya doesn't take the news of stolen clients lying down. Meanwhile, Jessica decides to go it alone; and Charlie reaches out to a protégé for help.
Ray takes a nervous walk down memory lane when he thinks a former student might be a new client. Meanwhile, Jessica starts working in the office of the doctor who was married to Ronnie's mistress; Tanya pays a price to be reunited with her mentor; and Lenore makes Sandee an offer she can't refuse.
Charlie gives Tanya advice about how to handle Lydia; Jessica finds a kindred spirit in Matt; Sandee's demands for Lenore become more extravagant; Ray and Tanya hatch a plan to rid themselves of a troublesome client.
Jason misses a date with a client, which draws Lenore's wrath; Darby is fed up with her home life; Lydia gives Ray and Tanya an unforgettable experience after he announces a big career move.
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 calls on the mother of Charlie's baby to help find him after he skips bail; Lenore makes it her mission to destroy the Wellness Center; Sandee coaches Jason on how to make his move; Ray worries that he's lost his magic touch with women, including 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.
In the third-season finale, 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.