His name is Ray Drecker; high-school teacher by day, male gigolo by night. In Season Two of this hit comedy series, all hell breaks loose as Ray decides to add another pimp to the mix in the person of his teaching colleague Lenore Bernard.
Ray finds himself thinking about Jessica (having discovered his ex-wife was willing to hire a gigolo) and reaches out to her "to discuss the kids." Jessica, meanwhile, faces resistance from Darby when offering advice in the romance department, when the girl accuses her mother of living her life through men.
Ray (Thomas Jane) irritates Lenore (Rebecca Creskoff) and risks losing a client by giving Claire (Kathryn Hahn) marriage advice. Tanya (Jane Adams) tries to prove she can land a big fish for Ray after being humiliated by Lenore during a meeting with a 60-year-old widow. Ray uses his sex earnings to pay for the school baseball team’s transportation to away games, raising Mike’s (Gregg Henry) suspicions. Jessica (Anne Heche) embarrasses Darby (Sianoa Smit-McPhee) by crashing an eat-in protest outside a fitness gym. At the end of a long day, Ray reconsiders accepting a gift delivered by his neighbor’s wife, Yael (Alanna Ubach).
Spurred by criticism from Damon (Charlie Saxton) and Darby, Ray tries to prove he’s not an insensitive ex-jock. Seething from the demands of her new boss at work, Tanya turns to Charlie (Lennie James) for advice on how to deal with an even more irritating problem: Lenore. Meanwhile, Jessica feels the pinch of the economic downturn, but can’t stomach Ronnie’s (Eddie Jemison) remedy.
Ray gives Lenore an ultimatum, and probes Tanya about the possibility of cutting ties with her fellow pimp. Disturbed that Damon has defiled the school baseball diamond, Ray considers Tanya’s suggestion that his son find a new hobby to shake him out of his recent doldrums. Ignoring Ray’s warning, Lenore offers Jessica advice in dealing with Ronnie. On his way to meet a new client, Ray has to think on his feet when he runs into Mike in a hotel lobby.
Tanya (Jane Adams) lands Ray (Thomas Jane) the “white whale” of clients, but an emergency involving Damon (Charlie Saxton), which began with his debut at a poetry slam, threatens to derail the date. With Mike (Gregg Henry) at the end of his teaching rope, Ray decides to promote him to co-manager of the baseball team. Jessica (Anne Heche) is peeved with Ronnie (Eddie Jemison) for being overly suspicious.
Jessica turns to Ray for help with a rodent problem that may be imaginary. Rebuffed by Ray in her attempts to add Mike to her stable, Tanya gets guilt-management advice from Charlie (Lennie James), then goes to extremes to prove her success. Ray has difficulty thawing a client who is cold as ice.
A container of hummus puts Ray in the unenviable position of choosing cultural sides between Yael (Alanna Ubach) and new client Samara (Mozhan Marno). Already upset after squandering her recent windfall, Tanya catches Ray in a cover-up – and turns to Charlie for stress relief. Lenore (Rebecca Creskoff) seethes after learning of Tanya’s duplicity. Liz (Merrin Dungey) surprises Ray with a revelation about her personal life.
With his team’s future wracked by vandals, Ray agrees to participate in a student-alumni baseball game, but an unexpected warm-up session with Claire (Kathryn Hahn) threatens to put him on the disabled list. Fed up with Tanya’s greed and confused by Mike’s request for a donation, Frances (Roxanne Hart) doubts their affair. Jessica’s old itch resurfaces, prompting Ronnie to deliver a sideline ultimatum to her ex.
A bad day at school gets worse when Mike accuses Ray of betrayal. Ronnie vents his frustrations with Jessica at a dermatology banquet, sending his wife running for the exit. Empowered by confession, Tanya lashes out at Ray, Lenore and Horny Patty (Lauren Weedman).
Eyeing a possible second chance with Jessica (Anne Heche), Ray (Thomas Jane) contemplates a break from the business – but Lenore (Rebecca Creskoff) may not be willing to give him up without a fight. Emotionally frayed after separate encounters with Damon (Charlie Saxton) and Vera-Joan (Rhea Perlman), Tanya (Jane Adams) visits Frances (Roxanne Hart) and Ray to try to make amends. After getting a lift from Mindy (Amy Farrington), Ronnie (Eddie Jemison) returns home to find that Jessica has made a decision that could impact both their futures.