Marketing Ray as a high-end "happiness consultant," Tanya tracks down former law-firm colleague Lenore, who agrees to take Ray for a test ride in exchange for the names and numbers of wealthy women. Jessica's obsessive behavior grates on her kids, who push Ray to fix his fire-damaged house. A contractor promises Ray a "wolf pack" discount for repairs, but money mismanagement has Ray strapped for cash. That could change after Ray's session with Lenore - or so he and Tanya hope.

West Lakefield students choose "Coach Ray" to be the recipient of their fall fundraising efforts, but Ray sees their pickle-jar donation as an embarrassing metaphor for his downward spiral. All is not lost, however - Tanya has a couple of leads that could jumpstart Ray's gigolo career. But is Ray ready, willing and able enough to follow through? Meanwhile, Damon is shattered when he rushes to his sister's defense during drive-in family night, only to learn that Darby doesn't want his help.