Season 2

Ray, Tanya and Lenore's new partnership starts inauspiciously when Ray "holds back" during a tryst with a pregnant client.

Ray irritates Lenore and risks losing a client by giving Claire marriage advice. Tanya 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 suspicions. Jessica embarrasses Darby 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.

Spurred by criticism from Damon 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 for advice on how to deal with an even more irritable problem: Lenore. Meanwhile, Jessica feels the pinch of the economic downturn, but can't stomach Ronnie's 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 finally gets Francis to agree to dinner with Ray and Lenore is continuing to be a pest as usual. Ray can tell that Mike is struggling to not continue with his life and tells that he needs to look at himself and tell himself that he is wonderful. Damon goes back to the Poetry Bar and embarrasses Darby after which he has a performance "enhancing" scone and sees Jessica and Ronnie naked. Ray has to choose whether to cancel on the big client or his son who needs him.

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.

Ray must choose sides between Yael and a new client; Tanya turns to Charlie for stress relief; Lenore learns of Tanya's duplicity; Liz surprises Ray with a revelation about her personal life.

Ray's unscheduled appointment with Claire threatens his participation in a student-alumni baseball game; Frances has doubts about her affair with Mike and her business relationship with Tanya; Ronnie delivers a stern message to Ray.

Mike accuses Ray of betraying him; Ronnie has a big fight with Jessica at the dermatologists' banquet; Tanya gets things off her chest when she goes into confessional mode and tells Ray, Lenore and Horny Patty exactly what she thinks of them.

Ray considers leaving the business; Tanya is emotionally frayed after encounters with Damon and Vera-Joan; Jessica makes a decision about the future.