Summary: Grace's ex-boyfriend Nicholas shows up with his girlfriend Paula and asks Grace to join them in a threesome. When Grace tells Karen and Will, they laugh and poke fun at Grace. Karen calls her "Prudence McPrude, the Mayoress of Prudie Town". Neither believes Grace would actually participate in a threesome, so she decides to go ahead with it.
Grace arrives at the motel, bundle up and ready to go. The threesome starts off nicely enough, with both Nicholas and Paula trying to help Grace feel comfortable. But when the couple's arguing threatens to end the threesome, Grace explodes, yelling at the two about how much she's a "good girl" and she had to psyche herself up to have sex with them. She orders Nicholas and Paula to "kiss and make up, because the three of us are gonna GET IT ON!" This turns both of them on, but Grace realizes that she's a "good girl" and doesn't want to do it anymore.
However, this is not how she tells it to Karen, who leaves the office in disgust.
Meanwhile, Jack starts working at the Banana Republic as a sales associate and sees an intelligent cute guy, Matthew, whom he wants to talk to. But Jack is worried that he won't seem smart enough to Matthew. He convinces Will to feed him lines through his headset while Will hides in a changing room.
At first, the plan it works great. Soon though, Will starts taking a personal liking to Matthew. He begins having a conversation with Matthew (through Jack), who gets bored with the topics they discuss. When a woman accidentally enters the changing room Will's in and Jack ends up shouting "Get out of here, you silly woman!", Matthew decides he should leave.
Jack of course, decides he doesn't want Matthew anymore and lets him down gently. Matthew tells Jack he's interested in somebody else, which Jack doesn't buy. As Jack goes off to hit on another customer, Matthew enters Will's change room and hands him his business card, telling Will to call him.
Quotes
KAREN (ANSWERING PHONE): "Grace Adler Designs." (GIGGLES) "Hey there, big daddy." (LAUGHS) "What are you up to, you little dirty dirty?"
GRACE: "Ok, hang up, hang up." (INTO PHONE) "Hey, sexy. Oh, hi, Dad."
KAREN (to JACK): "You know...This isn't working. This is gonna interfere with our friendship. I work a 40-hour month for what's-her-name, and I always make time for us. Come on."
JACK: "Karen-- I can't, all right? But I promise. Nothing's gonna change between us. Hey, I'll come over later, and we'll short-sheet Rosario's bed."
KAREN: "Okay. Maybe we can take a big bubble bath together."
JACK: "Nothing would give me more pleasure than to sponge-clean the Beaverhausen."
WILL (to JACK): "Hey. I just received a message saying you have a new job and you're going to buy me dinner. There's, like, 18 things wrong with that sentence."
GRACE (to WILL and KAREN): "Hey, I have been known to get a little crazy in the boudoir. Some might even call me...kinky."
(WILL AND KAREN LAUGH)
GRACE: "Hey!"
WILL: "Sweetheart. People who are truly kinky never use the word kinky."
KAREN: "And who the hell says 'boudoir'?! 'Hey, hey. Look at me. I'm kinky, and I'm in the boudoir.'"
(WILL AND KAREN LAUGH)
GRACE: "I've done a lot of crazy things. I once had sex in the kitchen."
WILL: "Ooh. What are you-- A rock star?"
(WILL AND KAREN LAUGH)
GRACE (to WILL): "I have clients coming. Get out."
WILL: "If I don't, are you gonna spank me, kinko?"
GRACE: "Get out!"
WILL: "Whoa! If I hear anything like that in the boudoir, watch out!"
(following quote submitted by Catwoman)
KAREN (to GRACE): "I love you like the mother I had committed against her will."
KAREN (to GRACE): "You are Prudence McPrude, the Mayoress of Prudie Town."
KAREN (to GRACE): "So, come on. How was your sexcapade, honey? Were you the ham in a philharmonic sandwich? Did you roll over for Beethoven?"
WILL: "You want me to tell her?"
GRACE: "No, that's ok. I'm not ashamed." (to KAREN) "It was fantastic. There were so many arms and legs everywhere, Hindus were praying to us."
KAREN (SCOFFS): "Oh... You sleazy skank."
GRACE: "What? Karen--"
KAREN: "I gotta take the rest of the day off. The air in this room is ripe with filth. For God's sake, Grace. I'm a mother!"
Did You Notice...
~We learn more about Karen's mother, when Karen reveals that she had her mother commited against her will.
~Will and Karen were being nice to each other in this episode.
~Will's line, "There's, like, 18 things wrong with that sentence" is similar to Karen's line in "Polk Defeats Truman", "Honey, do you know how many things are wrong with that sentence?"
~Jeremy Piven, who plays Grace's ex, Matthew, starred on "Ellen" as Spence. "Ellen" was a ground-breaking TV show, the first to feature a gay lead character, and which paved the way for shows like "Will & Grace",
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