S2, E15: When Will (Eric McCormack) is set up on a blind date (guest star Michael E. Rodgers) by his boss (guest star Gregory Hines), he has internal debates on whether or not to go. Of course, Jack (Sean Hayes) gives Will advice on how to be a good blind date. Meanwhile, Grace (Debra Messing) continues to struggle with her wimpy boyfriend Josh (guest star Corey Parker) as Karen (Megan Mullally) doles out some typically un-wanted advice.