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.
Tanya tests the market for her business’ services among her colleagues; Damon’s devotion to a friend in detention puzzles his father; Jessica gets advice from Lenore.
Ray needs relationship advice from Tanya; Lenore offers Tanya some unsolicited marketing tips; a barbecue at Jessica and Ronnie’s puts Ray in an awkward place.
Ray deals with his developing feelings for Jemma. Meanwhile, Tanya meets someone new who may help her overcome her writer’s block. As Ray is scouting for potential customers at a farmer’s market, he bumps into Jessica who invites him over...
Ray accompanies Jemma to a couples counseling session without the prior knowledge of Tanya, who later confronts Jemma for bypassing her escort service protocols. Meanwhile, Jessica wants to know their real financial situation from her husband. Ray coaches...
An unhappy client wants to revisit a role-playing fantasy; Ray tries to capitalize on Jessica’s frugality with the promise of a car for Damon and Darby; Tanya reluctantly goes on a date with Floyd.
The students of Lakefield vote for Coach Ray as their recipient for the fundraiser bur Ray finds it embarrassing. Tanya has other ideas to boost Ray’s career as a gigolo. Damon is left reeling when his sister rejecting his help.
Ray’s neighbor, Howard Koontz, files a public indecency complaint against him after he takes a leak at the lake. Tanya and Ray try to track down Lenore and recover his missing wallet. Floyd Gerber invites Tanya to a business dinner. Jessica finds herself...
Ray fears for his teaching job as he is called to the Principal’s office. He and Tanya push through with their planned business. Hoping to set up their clientele, Tanya enlists a former colleague who has upper-class contacts that are potential customers....
After a tragedy struck Ray and his home, he is forced to seek an alternative source of income as his kids move in with their mom. With his ex-wife unwilling to help, he enrolls in an entrepreneurship seminar where he learns to discover the winning tool...