Ray is driving down a highway talking on his phone to the parent of one of his basketball players. The lady is complaining that Ray hasn't let her bundle of joy start on the Varsity squad. Ray explains that the kid is only a sophomore but he has a lot of promise. The lady says that, just like she did with her kid's brother, she'll nag him until he lets the kid play. Parents + athletics = all manner of craziness. Ray sees something on the side of the road and stops his car. He tells the lady on the phone that he'll have to get back to her. He backs up and we see that a lady is trying to change her tire.
Ray asks if he can help and the lady says that's not necessary, unless he's an expert. He is, apparently. She asks him if he likes helping damsels in distress and he replies that, if she were a fat-ass truck driver, he would have kept driving. She laughs it off, and he asks her if she'd like to get some lunch. Next time we see these two, they're boffing in the bathroom of some place (perhaps an Applebee's). Ray is all business and she seems to like it.
Cut to Ray doing chin-ups at Tanya's house while she is shredding zucchini (that is not a euphemism). She tells him that the lady didn't like her session. That's the lady from before. She was a client. Ray says she's acting like someone at a restaurant who eats all of their food then pretends there was a hair on the plate. Tanya smiles and tells him that he can't always hit a home run. Lenore had explained that the woman had been in a string of bad relationships, and she felt that their meeting felt like a fantasy for him as opposed to for her. Tanya suggests that she concentrate more on the woman's mind. Her suggestion is relevant because the woman wants to do it again -- she wants a do-over.
We see Ray drive up beside the woman on the side of the road again. They rush through the introduction. Next, they're sitting at a restaurant and Ray asks her what her name is. It's Jemma. He says his name is Randall. He tells her that he's a book editor and she asks him what kinds of books he edits. Frustrated, he says that he works on "good" books. Then, he elaborates and tells her that he doesn't care if something's going to be a bestseller or not. He likes quality. She says that she's a sellout, because she works in an ad department. He then asks her if she would like to go to a movie. She would, but she has a boyfriend. Ray doesn't know the next line. He just sort of stammers and she leaves to meet this boyfriend.