Loose Lips Sink Relationships

S4 E5: In a sneaky ploy to bum a night off from work at Barney's department store, a conniving Jack plays matchmaker and takes advantage of his geeky female supervisor's (guest star Parker Posey, "Best In Show") interest in Will (Eric McCormack) - while mindful of Will's fantasy of modeling in the store's catalogue - and he parlays their mutual desires into a "date," even though his unsuspecting friend doesn't have a clue of her intentions. Elsewhere, Grace (Debra Messing) goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's (Emmy Award-winning guest star Woody Harrelson, "Cheers"). Megan Mullally also stars.