"And suddenly, I wanted to win. I wanted to win while she watched." -RayIt's a cliche of stories about prostitutes -- let's call it Pretty Woman Syndrome -- that the whores all dream of finding a rich, handsome, kind john who will whisk them away from this awful life. This storyline with Jemma isn't exactly the gender-flipped version of that, but it's similar.
What we're seeing is Ray's continued struggle to accept the realities of the business he has chosen. He seems startled when Jemma agrees that he's a whore, thinks nothing of revealing his true identity to her, and even offers to stop charging her. It's one thing for him, it seems, to play the part of the escort when the client looks like Margo Martindale -- when there would be no chance of intimacy outside of this professional arrangement. But when she looks like Jemma, and when the games Jemma plays start to turn Ray on, then... well, then Ray starts acting like she's his girlfriend. And that's dangerous territory, whether or not Jemma (who's crazier than Ray wants to admit) decides to reveal his secret identity to the world.
But while his fixation on Jemma isn't smart, or emotionally healthy, it did have the odd benefit of making him a better basketball coach for a few minutes. Actually, we've seen for a few episodes now that when Ray's side career is going well, it seems to bleed into his regular life, making him happier, more confident and simply better.
As with "Do It, Monkey," Ray's struggle to play along with Jemma's fantasies -- particularly the couples therapy scene -- helped keep the comedy quotient high, as did Tanya's predictably sad attempt to enforce the rules of her agency. Not that I want to make the "Breaking Bad" comparisons every week (especially since Colette Burson said at press tour that she's interested in different things than that show), but in the context of that show and the performance of Bryan Cranston, I can come to believe that a dweeb like Walt White could turn into a physically intimidating criminal genius. On this lighter show, with the funny but intentionally pathetic performance of Jane Adams, I can't envision a future where Tanya is putting the fear of God into clients with her pimp hand. So either she's going to have to come up with a more clever method of enforcing the rules, or she's going to have to hire some muscle (or have Ray take on some of the pimping duties).
One final note: Tanya meets Ray's family, and makes a comment about how she can kinda/sorta/maybe see the resemblance between Ray and Damon. So while the cast and producers are sensitive to complaints about the casting of the two kids (mainly because you can read an undercurrent of "why aren't they better-looking?" to those complaints, whether it's intended or not), clearly it's something they're aware of as well, and willing to acknowledge within the context of the show.
What did everybody else think?