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.

Ray is frustrated when an unsatisfied client asks for a do-over of her "damsel in distress" roadside fantasy. With times tight for Ronnie and Jessica, Ray hopes to one-up his ex by promising to buy a car for the twins. Tanya goes on a pity date with Floyd and is surprised by the outcome.

Tanya takes umbrage with Jemma for bypassing her service to set up "dates" directly with Ray. Still upset about a decision to put down her dog, Jessica confronts Ronnie about their finances, learning that times may not be as tough as heʼs made them out to be. After Jemma prods Ray to open up about himself, he gives his basketball team an inspiring pep talk.