A client who is unhappy wants to revisit a role-playing fantasy; Ray promises a car for Damon and Darby, to capitalize on Jessica's frugality. Reluctantly, Tanya agrees to go on a date with Floyd.

Tanya objects to the break in protocol after Jemma bypasses her to set up "dates" directly with Ray. Jessica confronts Ronnie about their finances, but he refuses to give her a straight answer. After Jemma prods Ray to open up about himself, he gives his basketball team an inspiring pep talk.

Ray starts to fall for Jemma, which clouds their professional relationship. Tanya receives unexpected help for her writer's block. Jessica invites Ray to a family dinner.

After standing him up, Jemma tells Ray they should take a break, and Ray seeks out Tanya for advice on women. Ray finds himself in an uncomfortable situation at Jessica and Ronnie's family barbeque.