Ray's new co-partnership with Tanya and Lenore gets off to a rocky start when he "holds back" during a tryst with Claire, a client, so he turns to Tanya for advice. Later, Ray and other teachers picket the school in anticipation of summer layoffs. Jessica, already filled with doubts about her marriage to Ronnie and refusing to take calls from Lenore after her experience with the no-show gigolo, is stung by criticism from Darby and Damon. Looking to get an edge on Lenore and regain Ray's trust, Tanya ventures into a tough neighborhood for liberating pimping advice from...
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 lands Ray the "white whale" of clients, but an emergency involving Damon, which began with his debut at a poetry slam, threatens to derail the date. With Mike at the end of his teaching rope, Ray decides to promote him to co-manager of the baseball team. Jessica is peeved with Ronnie 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, 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 position of choosing cultural sides between Yael and a new client. Tanya catches Ray in a cover-up--and turns to Charlie for some stress relief. Lenore seethes after learning of Tanya's duplicity.
With his teamʼs future wracked by vandals, Ray agrees to participate in a student-alumni baseball game, but an unexpected warm-up session with Claire threatens to put him on the disabled list. Fed up with Tanyaʼs greed and confused by Mikeʼs request for a donation, Frances doubts their affair. Jessicaʼs 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 hills. Empowered by confession, Tanya lashes out a Ray, Lenore and Horny Patty.
Eyeing a possible second chance with Jessica, Ray contemplates a break from the business - but Lenore may not be willing to give him up without a fight. Emotionally frayed after separate encounters with Damon and Vera-Joan, Tanya visits Frances and Ray to try to make amends. After getting a lift from Mindy, Ronnie returns home to find that Jessica has made a decision that could impact both of their futures.