Will & Grace - Season 4 - Eps 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 interest in Will, while mindful of Will's fantasy of modeling in the store's catalogue. Jack 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.
About Will & Grace

Title: Will & Grace
First Air Date: 1998-09-21
Last Air Date: 2006-05-18
Status: Ended
Rating: 6.8/10 (from 499 votes)
Language: EN
Seasons: 9
Total Episodes: 194
Network: NBC
Genres: Comedy
Production Companies: NBC Studios, KoMut Entertainment, 3 Sisters Entertainment, Universal Television
Synopsis
Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.
Cast

Eric McCormack
Will Truman

Debra Messing
Grace Adler

Sean Hayes
Jack McFarland

Megan Mullally
Karen Walker