Written by: Dmitry Lipkin & Colette Burson
After another teacher loses his job and everyone worries about their own security, Ray is called to the principal's office. While sitting and awaiting his impending doom, Ray ponders the series of events that have led to this moment:
Jessica's attempts to recapture closeness with Damon and Darby have the opposite effect, and they pressure Ray to bring them back home. Now Ray needs an infusion of cash to speed up his house repairs.
After hearing Tanya's pitch, Ray is dubious about the viability of their Happiness Consultant venture, but Tanya reassures him with her alleged connection to women with disposable income. Tanya contacts Lenore (her former colleague and now successful personal shopper) in an effort to drum up business, but Lenore insists on sampling the product before recommending it to her rich clients. Lenore puts Ray's stamina to the test and he delivers until exhausted, he passes out in her home. Waking up late for work the next morning, Ray has to rush to work, unable to find his wallet and his underwear.
Back in the principal's office, Ray is relieved to hear that he's been called in because of his pep talk, and must watch his language in serving as a moral example to his students. His day job safe for the time being, Ray speaks to Tanya to relay that his moonlighting gig went well. Encouraged by his report, Tanya promises they are on their way to success and that his wallet is on its way back too.