Girl Trouble is the 4th episode of the third season and the 50th overall.
Grace is appalled when an impressionable new intern suddenly emulates Karen and takes on her brass persona, causing the office to go haywire. Meanwhile, Will and Jack muck up a gay-sensitivity seminar for local cops.
Grace gets a young intern in her office who worships Grace and her work, but Grace's delight is short-lived when the intern quickly remakes herself in Karen's image.
Capital G! Arbage!
Meanwhile, Will is putting together a skit for gay sensitivity seminar for the local police, and asks Jack to act in it along with two lesbians Jack doesn't get along with. Jack manages to remain polite to the lesbians as an acting challenge from Will, but when Will makes fun of Jack's character voice, Jack loses it and insults the lesbians in front of the police audience. Jack and Will end up in a screaming fight that they are terribly embarrassed about, but it turns out that their real insults are actually educational as well.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Natasha Lyonne (Gillian)
- Suzanne Krull (Terry)
- Henriette Mantel (Annie)
- Christopher Darga (Officer Kirk)
- Louis D. Giovannetti (Officer Bob)
- This is the only episode to never have been repeated during the show's prime-time run (not counting the current season or syndication).
- Producer/Creator Max Mutchnick had this to say about Jack's harsh language: "In cutting this show--and I regret this cut--we took out the explanation of why Jack doesn't like these two women. On [the original] film, Jack says, 'They don't like me,' and Will says, 'That's because you were caught stealing twine from their kite shop.' I'm recutting the show for syndication, and I'm including that back story because I want it to be very clear that this was Jack's issue with these two women. It had nothing to do with their being gay."
- One of Natasha Lyonne's first TV appearances. She would later gain recognition for her roles in the LGBTQ-themed Orange Is the New Black and the American Pie film series.
- Will does his accents again, a habit introduced in the episode The Buying Game.
- Jack refers to Terry and Annie as "Starsky and Butch", after the eponymous characters of the 1970s show Starsky & Hutch. During the first season episode Boo! Humbug, Jack dresses up as Hutch.
- Upon finding out there are lesbians in Will's script, Jack exclaims "Billie Jean King! There are lezzies in this!". Will responds, "Martina Navratilova, yes, there are!". King and Navratilova are famed tennis players who both came out as lesbians at the peak of their careers during the 1980s. Navratilova later appears as one of Karen's romantic partners in the episode Lows in the Mid-Eighties.
- When Jack claims that Shakespeare used to cast men to play lesbians in his plays, Will sarcastically mentions the "coven of high school gym teachers in Macbeth". This is a reference to the Three Witches at the beginning of Macbeth, and a play on the stereotype that lesbians are usually gym teachers.
I've got something tough to tell you. Uh, I'm fabulous, ok? I'm an incredible dresser, I've got buckets of money, I'm a hoot and a half, and I got a killer rack. Do you get what I'm saying? — Karen