Joe, Q, Prince Herb, and Murr recruit new senior executives for their companies and then jump into the dating pool. Plus, the big loser gets an opportunity to show off his musical chops to a captive audience.

Murr, Joe, Sal, and Q participate in the documentary filmmaking process. Later, they read a teenager's diary to surprise and delight strangers. And when they lose, they find motivation to do better next time.