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 starts to fall for Jemma, which clouds their professional relationship; Tanya receives unexpected help with her writer’s block; Jessica invites Ray to a family dinner.
Tanya reaffirms her status as Ray’s pimp to Jemma, who inspires Ray to give his basketball team a rousing speech; Jessica gets to the bottom of her family’s financial situation with Ronnie.
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.
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.
Howard Koontz a nosy neighbor of Rays’s accuses him of public indecency. While Damon and Darby want their father. Ray and Tanya struggle with their partnership until a plan reignites their dreams.
Tanya enlists the help of a former colleague Lenore to help Ray in exchange for names and numbers of rich women.
After a slightly inappropriate pep talk to the West Lakefield High Wolves, head basketball coach Ray Drecker fakes a kidney stone attack, leaving assistant coach Mike to take the helm during a losing streak. On his way to meet his first client for his...