When Will is set up on a blind date by his boss, he has internal debates on whether or not to go. Of course, Jack gives Will advice on how to be a good blind date. Meanwhile, Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice.
Quest roles:
Jo Marie Payton(Mrs. Freeman), Gregory Hines(Ben Doucette), Corey Parker(Josh), Michael E. Rodgers(Charlie), Kathleen Marie Archer(UPS Woman), Brian Gattas(Waiter)