Thomas Jane stars in this HBO comedy series about a high-school teacher who rides his plus-sized package to a better life. With his world in disarray in Season One, Ray Drecker decides to finally take control of his life...by becoming a male gigolo.
Ray seeks guidance to help him with his problems and his first task is to find a winning tool for financial success. Tanya, also attending the self-help group, helps Ray.
Tanya enlists the help of a former colleague Lenore to help Ray in exchange for names and numbers of rich women.
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.
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 ends a call from an angry mother about her son's position on the basketball team to pull over and help an attractive woman with a flat tire. He invites her to lunch at a nearby cafe, and they end up having rough sex in the bathroom. Turns out she's a trick, and Tanya explains to Ray later that the customer wasn't happy: She wanted more of a female fantasy than a male fantasy. The client, Jemma, pays for a do-over in which Ray shows up as Randall, a book editor. This time, when he asks her on a date she says she has a boyfriend and takes off. Debriefing, Tanya explains Ray was supposed to stop her from leaving.
Jemma brings Ray (aka "Jim") to a couples counseling session and confronts him about his money issues. When Ray is unsure how to respond she blows up, and he blurts out that something about Jemma must be a "big fat turn off." She storms out, but waits calmly outside to hand over his fee, refusing any further explanation. When Ray tells Tanya that Jemma called him directly, Tanya objects to the break with protocol but he begs her not to interfere.
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 leaves another message for Jemma as he continues to wait on the dock for her. Finally, she calls to say she's not going to make it -- they need a break. Jilted, Ray shows up at Jessica's and Ronnie's for family dinner and after observing some tension, corners Ronnie and demands to know how he "got the girl."
Ray is disconcerted to learn that Damon is exploring a homosexual relationship with his friend Powell. Meanwhile, he continues to feel mounting financial pressures, but Tanya is struggling to find clients who can afford his fees. After feedback from Horny Patty that Ray is like cocaine (expensive and addictive) and she needs crack (same high, half the price), Tanya urges Ray to consider discounting his services.
Tanya comes to Ray in the middle of the night for help when her apartment is infested with flies, concerned the universe is trying to tell her she's "dead meat" -- first Pierce disappears to Cuba, and now she's concerned Ray is going to disappear on her too. Ray assures her he's not going anywhere. However, when he meets Lenore for lunch and she points out the rich clientele she can line up for him, he suggests a partnership with Tanya. Lenore insists he has to choose just one pimp.