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.

Tanya is dismayed when a "satisfied" customer says she won't be using Ray's services again. Later, Tanya pitches Happiness Consultants to other women in her office, with mixed results. Damon goes to after-school detention to hang out with his androgynous friend Powell, leaving Ray baffled. Lenore gives Ray lessons in branding and, after a chance encounter at a department store, offers Jessica lifestyle advice.