Episode 76 of "Will and Grace"
s04e05 Loose Lips Sink Relationships

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 interest in Will—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 goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's.