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.