Tanya takes umbrage with Jemma for bypassing her service to set up "dates" directly with Ray. Still upset about a decision to put down her dog, Jessica confronts Ronnie about their finances, learning that times may not be as tough as heʼs made them out to be. After Jemma prods Ray to open up about himself, he gives his basketball team an inspiring pep talk.

Ray's relationship with Jemma gets murky when he begins to develop real feelings for her. Tanya meets a hipster who sets out to help her get through her writer's block. Looking to land new clients at a farmerʼs market, Ray runs into Jessica, who invites him to dinner with Ronnie and the twins. Ray's finds himself in a potential quid pro quo situation with Yael, the wife of his despised neighbor Howard.

After standing him up, Jemma tells Ray that maybe they should take a break, and Ray seeks out Tanya for advice on women. Meanwhile, Tanya finds her new boyfriend Pierce to be a man of mystery. Attending a family barbeque at Jessica and Ronnieʼs, Ray finds himself in a (predictably) uncomfortable place. After seeing her classified ad, Lenore gives Tanya some unwanted feedback on her marketing strategy, which leads Tanya to take a more personal approach.