Last Ex to Brooklyn is the second episode of the sixth season and 118th overall.
Leo invites over her ex-girlfriend Diane for dinner; Grace invites Will, Jack and Karen. Things get painfully awkward for Grace when she learns that Diane and Will already know each other.
Grace and Leo host a dinner party to which his ex-girlfriend Diane is also invited. Diane, who is a writer for Vogue finds herself a new friend in Grace even giving her an expensive Hermès Birkin bag.
OH. MY. GOD.
Things turn difficult when Will, Jack, and Karen arrive and they all find out that Diane is the same girl Will slept with during college, right after he broke up with Grace. This knowledge of their past drives Grace jealous, realizing that the woman Will slept with is funny, beautiful, and smart. Leo then becomes indignant that his wife seems more jealous of Will and Diane considering he had an actual relationship with Diane.
While having dinner, things get even more tense especially after Karen asks Diane who was better in bed and she answers that Will was better, and that it was the only time she ever had an orgasm in her life.
Diane and his history with Will is first referenced in the flashback episode Lows in the Mid-Eighties. She was briefly seen on-screen, played by crew member Lisa Borgnes.
Mira Sorvino's then-boyfriend Christopher Backus appears later in the season as Adam in the episode Looking for Mr. Good Enough. Sorvino and Backus would marry shortly after the season ends in 2004.
Cultural references[]
The bag that Diane gives to Grace is a red Birkin manufactured by Hermès, famous for being extremely expensive, usually valued from $11,900 to $300,000.
Leo and Diane were once caught having sex by former New York City mayor Ed Koch.
Karen compares Grace's "twinhood" with Diane to that of actors Randy Quaid and Dennis Quaid, who are brothers albeit with different public images.
Quotes[]
You're a gorgeous redhead, I'm an adorable blonde. But we know we have something in common: brown hair.—
Diane, to Grace
I mean at the moment, I've had sex with everyone in this apartment... including myself.—
Leo, when his ex-girlfriend arrived
Diane:
I hope you don't mind me judging you solely on the basis of your looks.
Grace:
Oh, please. How else would you judge someone?
Grace:
I've been on a waiting list for that bag for two years, you bitch. I can say that, right? We're in that place?
Diane:
Oh, we're way past that place, you dirty skank.
—getting to know each other
The Hermès Birkin bag! I've been on that waiting list for two years... for my mother.—
Will
Grace:
I'm not jealous. And I'll tell you why I'm jealous. Because I'm not jealous.
Leo:
You're not making any sense.
Grace:
Oh, and all of the sudden, you're the President of the things that make sense?
Karen:
I like you. Wanna make out?
Diane:
I like you too. Let's see how the evening goes.
Diane:
Hey, um, can we open the $25 bottle of wine I brought? 'Cause I think we're done with the $6 stuff.
Leo:
Yeah, it's my fault. I thought two bottles per person was going to be enough.
Karen:
Maybe if we were in high school.
Leo:
You and Will, huh?
Diane:
Yep, me and Will.
Leo:
And me and you, huh?
Diane:
Yeah. Me and you. And maybe later me and Karen.
Leo:
Why do you care that Diane's had Will's kabobs, but you don't care that she's had mine and I've had hers?
Jack:
Silly. Diane is a girl. She doesn't have kabobs. She has a kagina.
Karen:
And nice katits.
—euphemisms at its finest
Grace:
She is beautiful. She's funny. She's smart. She's like my twin.
Karen:
Yeah. Right honey. Just like Randy Quaid is Dennis Quaid's twin.
Grace:
Nobody finds you interesting.
Diane:
Except your husband and your best friend?
Will:
Maybe it's just as well you never did take a ride on the Truman train. That coulda ruined you for life.
