Loose Lips Sink Relationships

Jack asks his new boss Dorleen for a day off
Jack asks his new boss Dorleen for a day off
Title “Loose Lips Sink Relationships”
Episode # 4.05 (72)
Season # 4
Original Airdate 25-Oct-2001
Writers Kari Lizer
Producers David Kohan & Max Mutchnick and James Burrows
Director James Burrows

Plot Synopsis

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.


  • Eric McCormack (Will Truman)
  • Debra Messing (Grace Adler)
  • Sean Hayes (Jack McFarland)
  • Megan Mullally (Karen Walker)

Guest Cast

  • Woody Harrelson (Nathan)
  • Andrew Rosenbach (Terry)
  • Parker Posey (Dorleen)


  • Jack gets a new job at Barney's New York (the Banana fired him).
  • This episode introduces Parker Posey as Dorleen, Jack's boss at Barney's.
  • Credited in this episode as "Barney's Employee," Andrew Rosenbach's character gets a name in episode #4.25.




Viewer Rating


Airdates & Ratings

10/25/20019:00 PM10.8/16%#15
01/03/20029:00 PM08.2/12%#16
08/08/20029:00 PM05.5/10%#23