Grammy nominated jazz musician Jeff Koz, 49 (and the brother of famous jazz musician Dave Koz), joins the Millionaire’s Club in the wake of his recent divorce. Jeff’s desire for a wild woman prompts Patti to diagnose him with “Divorced-dad-itus," an affliction that forces a man to make inappropriate dating choices.

Returning for another go around with the Millionaire’s Club is last season’s lovable letch, Harold Wrobel. For the past year, Chelsea has been trying to find a match for Harold. Though in his late forties, Harold insists upon dating women in their twenties. Patti decides to take drastic measures to help Harold get over his narcissistic ways by giving him a “dating intervention." Patti and Chelsea play “bad cop, worse cop” until Harold storms away. However, he ultimately returns, knowing that Patti is his only hope for finding true love.

Patti decides not to throw a mixer party, which she usually does for her millionaires. She feels it will be better if the two men see her recruiting process and hear the questions and answers between Patti and the girls. For their two dates, the men agree that they will each select a woman from the lineup of girls, and Patti will pick the other. The experience of watching Patti's interviews through a two-way mirror proves to be especially eye opening for Harold, who learns that women in their twenties don’t want to date men in their late forties.

Patti tries to set Jeff up with a gorgeous Harvard graduate, but Jeff chooses a tattoo laden, rocker chick. Jeff pulls out all of the stops by renting an entire mountain overlooking Lake Tahoe as a backdrop for their romantic dinner. Later that night, Jeff performs on stage with his famous brother, Dave Koz.