(Series Premiere) As a student at Detroit's West Lakefield High School, Ray Drecker was athletic, popular, and destined for success. Today, as a teacher and basketball 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 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 mom and her smug hubby, Ronnie Haxon (Eddie Jemison). Lonely, run-down and at wit's end, Ray decides to attend a local self-help class whose mantra is to identify a personal winning tool to market for financial success. After a not-so-fulfilling encounter with a fellow attendee--an ex-flame and would-be poet 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 behavior 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 low ebb after the Lenore debacle, sink further when his nosy neighbor, 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 the 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's 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 defense 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 times 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, Jessicaconfronts 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.