Will: I guess I could kiss heaven goodbye because it got to be a sin to look this good.

Carlton: Hey, Will, isn't that Jazz?
Will: Jazz, what are you doing here?
Jazz: Ssh. I'm on the list. They think I'm the Black dude from Mod Squad.

Will: Okay, next Saturday night?
Jackie: Bachelorette party.
Will: Christmas?
Jackie: I'm going home to Philly.
Will: Then New Year's Eve? Groundhog Day? Cinco de Mayo? Rosh Hashanah, huh?

Jackie: Will, you just hit on me from force of habit. Now, if you really wanna go out with me why not step to me like a man?
Will: Well, okay. So Jacqueline I wonder if you'd do me the honor of having dinner with me.
Jackie: Okay.
Will: "Okay"? "Okay" is all right if I offered you a government cheese sandwich, but I'm offering you a buffet of love, child.

Geoffrey: Would you like to have dinner with the children, sir?
Philip: Yes, that would be nice, Geoffrey.
Geoffrey: Too bad. They're not here.
Philip: Then why did you bring it up?
Geoffrey: If you don't care where your children are, sir, neither do I.
Philip: Okay, where are they?
Geoffrey: Sir, I could never betray their confidence. [Philip chuckles as he hands Geoffrey a note] They're at the Playboy Mansion. All except young Ashley. She's upstairs with her boyfriend.
Philip: Ah!
Geoffrey: That one's on the house.

Ashley: Hilary, are you really going to pose in that magazine?
Hilary: Why? Does it bother you?
Ashley: A little. I don't even like to get undressed in gym class.
Hilary: Ashley, your body is going through some changes and they may seem awkward and embarrassing but I promise you, it's completely normal. And the discomfort, it's only temporary.
Ashley: I know. I look great naked. It's just that I don't like a bunch of gooney people staring at me.
Hilary: Oh, you get used to it.

Will: [in the mirror] Well, hello, Hef. Oh, pshaw. Don't be silly. I'm glad I could come. Oh, Miss December. Oh, baby, I was gonna call you. Come here, girl.
Geoffrey: Excuse me, Master William if you can tear yourself away from your imaginary friend... a Miss Jacqueline's on the phone.
Will: Oh, I forgot all about Jackie. Look, G. G, G If you had to decide between going on a date with a girl you care about and going to the Playboy Mansion, which would it be?
Geoffrey: The fact you're even asking, Master William tells me that you really care about the lady.
Will: I guess I do.
Geoffrey: Admirable. Tell me, might this young lady have a terminal illness?
Will: No, G, of course not.
Geoffrey: Then may I point out, she'll still be here tomorrow.

Hilary: Wait a minute, Will. I think I'm having second thoughts.
Will: What do you mean?
Hilary: I don't know if doing the layout is worth having Daddy hate me the rest of my life.
Will: No, no, no, it's only the rest of his life. After them pictures come out, how much longer could he have?
Hilary: Will.
Will: I'm joking, I'm joking, I'm joking. I thought you wanted to do the pictures.
Hilary: Well, I do.
Will: I'm saying you can't just let your pop be pushing you around all the time.
Hilary: It would be so much easier if only he liked Playboy.
Will: Liked it? He's got issues in his bathroom from, like, 1964.

Will: Let's just go to the party.
Carlton: Freeze!
Will: Oh, look, the Little Republican Store must've opened.
Carlton: Good joke, Will. I'll laugh on the way to the party.

Hilary: Family, I have an announcement. Listen, Playboy is doing a pictorial on the prettiest weather girls from coast to coast. They're gonna call it "Warm Fronts." And they want me to be in it.
Philip: Absolutely not.
Hilary: But don't you even wanna hear what I have to say about it?
Carlton: You heard our father: No!
Hilary: Carlton, what do you care?
Carlton: Look, I will not be publicly embarrassed by a potential scandal.
Will: Now, now, don't get your Underoos in a knot, stumpy. Hilary knows what she's doing.
Hilary: Wait a minute, I haven't even decided-
Will: Quiet, Hilary. Work with me here, Hil. I can see it now: Long afternoons kicking back on a chaise longue watching full-body contact volleyball up at Hef's place.