Divorced dad and underpaid high school teacher Ray Drecker hatches an inspired plan to ride his 'winning tool' all the way to a more productive, debt-free life. First season of the comedy drama starring Thomas Jane.
Years ago, as a student at Detroit's West Lakefield High School, Ray Drecker was athletic, popular, and destined for success. Today, as a West Lakefield teacher and coach of the varsity basketball team (which is on an unprecedented losing streak), 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 lakeside home he inherited from his parents, Ray's sagging fortunes reach an all-time low when his twin children Darby and Damon, who had been living with him, move in with their mother and her smug hubby, Ronnie Haxon (Eddie Jemison). At wit's end, Ray decides to attend a local self-help class whose mantra is to identify a personal 'winning tool'. After an encounter with a fellow attendee - an ex-flame named Tanya Skagle (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.
In an effort to market Ray as a high-end 'happiness consultant', Tanya tracks down a former law-firm colleague named Lenore, who agrees to take Ray for a test ride in exchange for the names and numbers of wealthy women. Meanwhile, Jessica's obsessive behaviour grates on her kids, who push Ray to fix his fire-damaged house. A local contractor promises Ray a 'wolf pack' discount for repairs, but money mismanagement has Ray strapped for cash. That all could change after Ray's session with Lenore - or so he and Tanya hope.
Ray's fortunes, at a low ebb after the Lenore debacle, sink further when his nosy neighbour, Howard Koontz, accuses him of public indecency. Fed up with Jessica's maternal meddling, Damon and Darby yearn to go back to their dad's, but progress on Ray's home repair front remains stalled. Likewise, Ray and Tanya's frayed partnership seems to be dead in the water - until a last-minute proposal resurrects their dreams.
West Lakefield students choose 'Coach Ray' to be the recipient of their fall fundraising efforts, but Ray sees their pickle-jar donation as an embarrassing metaphor for his downward spiral. All is not lost, however - Tanya's got a couple of leads that could jump-start Ray's gigolo career. But is Ray ready, willing and able enough to follow through? Meanwhile, Damon is shattered when he rushes to his sister's defence during drive-in family night, only to learn that Darby doesn't want his help.
Ray is frustrated when an unsatisfied client asks for a do-over of her 'damsel in distress' roadside fantasy. With money tight for Ronnie and Jessica, Ray hopes to one-up his ex by promising to buy a car for the twins. Tanya goes on a pity date with Floyd and is surprised by the outcome.
Tanya takes umbrage with Jemma for bypassing her service to set up 'dates' directly with Ray. Still upset about a decision to put down her dog, Jessica confronts Ronnie about their finances, learning that times may not be as tough as he's made them out to be. After Jemma prods Ray to open up about himself, he gives his basketball team an inspiring pep talk.
Ray's relationship with Jemma gets murky when he begins to develop real feelings for her. Tanya meets a hipster who sets out to help her get through her writer's block. Looking to land new clients at a farmer's market, Ray runs into Jessica, who invites him to dinner with Ronnie and the twins. Ray finds himself in a potential quid pro quo situation with Yael, the wife of his despised neighbour Howard.
After standing him up, Jemma tells Ray maybe they should take a break. Ray seeks out Tanya for advice on women. Meanwhile, Tanya finds her new boyfriend Pierce to be a man of mystery. Attending a family barbecue at Jessica and Ronnie's, Ray finds himself in a (predictably) uncomfortable place. After seeing her classified ad, Lenore gives Tanya some unwanted feedback on her marketing strategy, which leads Tanya to take a more personal approach.
Tanya is dismayed when a 'satisfied' customer says she won't be using Ray's services again. Later, Tanya pitches Happiness Consultants to other women in her office, with mixed results. Damon goes to after-school detention to hang out with his androgynous friend Powell, leaving Ray baffled. Lenore gives Ray some lessons in branding and, after a chance encounter at a department store, offers Jessica some lifestyle advice.
Alarmed by a bad omen, Tanya ends up battling Lenore for control of Ray, who is worried about his future after hearing rumours from Mike about job layoffs at school. As Ronnie flirts with an old flame at work, an unfulfilled Jessica decides her battery needs a jump start. Ray finds a sweet surprise inside his home, courtesy of his local bees and his frisky neighbour. With a new relationship losing steam, Damon turns to Darby for advice and comfort.