Sandee comes to Tanya with an offer of Happiness Consultants pimping out Jason rather than continuing to work for Lenore. Charlie thinks it's a great idea for Tanya to do as Jason will do men as well as women when Ray will not. Ray's shoebox of money with about 5 grand goes missing and when it looks like Lenore didn't take it as expected there's no other really likely suspects. Ray sets up his own client at the suicide hotline where Lenore is volunteering while fixing his car. Tanya decides to go ahead with the deal even without Ray and she tells him about Charlie. Jessica is told by her boss that he and his wife are going to try to work things out. Ray goes to confront Charlie about him giving Tanya business advice and the first time seeing Lennie James and Thom Jane on screen with each other was a real treat to witness. After some harsh words Ray accepts that Jason will be a good asset for his retirement. He also goes to the mixer that Tanya planned where Tanya, Sandee, and Jason are all playing charades hilariously. Ray says he wants first dibs on jobs and 20% of everything Jason earns. Good for him to embrace that, it means less work for him and more money as Jason really could be an asset for the future of Ray and Tanya. Lenore comes to Tanya with her suspicions of Sandee having stolen Ray's shoebox which she ignores. Ray goes on a date with the client he set up with and Lenore discloses with Tanya that his new client is in face, a man. Good episode, especially one that made us acknowledge the fact that Ray is middle aged and won't be able to go on forever and possibly laying the framework for seasons to come.