Jack Sets Parker Posey And Will Up On A Date | Will & Grace | Comedy Bites Vintage

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Parker Posey joins the Will & Grace cast as Jack's new boss, Doreen, at Barney's New York, New York. Jack and Doreen agree to get her a date with Will, and Jack can choose his time off.

Will & Grace Season 4 Episode 5 '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 (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.

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