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As Ray mulls over his future, Lenore and Tanya fight for control over him. Meanwhile, Ronnie flirts with someone at work with whom he has a romantic past. Damon goes to his sister for comfort.

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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.

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.

anya 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.

A client who is unhappy wants to revisit a role-plying 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.

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.

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.

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.

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.