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.

After a satisfied client expresses no intent of reacquiring Ray's services, Tanya is disappointed and later begins to pitch their business to her co-workers. Damon hangs out after school with his bisexual friend in detention. Ray chances upon Lenore at the mall and receives lessons in branding.

After Jemma tells Ray she wants a break from their relationship, Ray goes to Tanya seeking advice. Tanya has to deal with issues of her own -- with her mysterious boyfriend Pierce and her ongoing marketing strategies for Happiness Consultants. Lenore can't keep from minding her own business and meddles with Tanya's. Ray, agreeing to a family dinner at Ronnie's, finds himself in an awkward spot.

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 for a family dinner.

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 a Saturday night basketball game with everyone in attendance.

Ray takes on an extraordinary client with unusual requirements. Ronnie himself is faced with financial difficulties, so his family needs to make some sacrifices, much to the dismay of Damon and Darby. Tanya attends her final session with Floyd.

Coach Ray hesitantly accepts West Lakefield students' fundraiser collection and uses it to buy a beam for his house. Tanya gets Ray more clients even though he's feeling a bit under the weather. Damon comes to his sister's rescue after Darby's break-up with Hammer.

Rays 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 a new object of affection while her kids still miss their father. Ray and Tanya get a break with a pleasant development in their business venture.

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. Meanwhile, Jessica is having trouble connecting with Damon and Darby, who wish to come home soon to their father.

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 which he hopes to bring him much-needed fortune. He also chances upon Tanya, who helps him in his newfound endeavor.