Ashley: Hilary, do you remember the first time you fell in love?
Hilary: Oh, this is important. Come. Come. Come. Sit. Sit. Sit. It was Lawrence Young, the most beautiful man at Bel-Air Prep. Oh! To put it simply, he was a god. He had been held back three years so he was really buff. Oh, he had the most amazing...
Ashley: Hilary. Hilary. Hilary, I get the picture.
Hilary: Oh, Ashley, are you in love?
Ashley: I think so. I feel like Derek's the one. I don't think I'll ever feel this way about anybody else.
Hilary: Oh, Ash, I am so happy for you. But long-distance relationships don't usually work out. I mean, look at the Little Mermaid. I mean, she was stuck in the sea and he was stuck on land.
Ashley: But they ended up together.
Hilary: Yeah, with the help of a lobster. You know a lobster?

Ashley: Hilary, can I talk to you for a minute?
Hilary: Not now, Ash, my show starts in five minutes. Uh-oh. Big-sister radar. It's important, isn't it? I can tell. I have, like, a third sense about these things.

Carlton: Oh, my God. What are we gonna do?
Will: This is what we're gonna do, we're gonna stop listening.
Carlton: You're right. Enough listening, time for action. She needs de-programming. We'll make her watch movies. Lots of movies. Doris Day movies. Now, there's a good wholesome role model. [sings] Que sera sera, whatever will be, will be... [talks] Wait a minute. "Whatever will be, will be"? What kind of devil-may-care message is that? The slut.
Will: Okay, Carlton. Carlton. Look, you need to calm down, all right?
Carlton: Look, we need to find a Yellow Pages. I'm calling a nunnery. It's late, so I'll need a 24-hour one.
Will: Carlton, man, we ain't even Catholic.

Carlton: I never liked the cut of that boy's jib.
Will: I'm not sure you should be admitting you've been looking at that boy's jib.

Will: How y'all doing?
Ashley: Hi. Is Derek here yet?
Will: Oh. He ain't coming.
Ashley: What?
Will: Yeah, it was a big accident, you know, out on the 605. Yeah, a jackknifed big rig, you know, spilled out a big load of, uh...
Carlton: Jackknives.

Carlton: Alright, let's stop beating around the bush.
Derek: Hey, man.
Carlton: You're playing chess, your rook has been blindsided by the queen's gambit. Now, you can play honorably, leave your bishop at home but protect your queen's virtue or you can take the sleazy road and castle your king and go right for the mate.
Will: And it's bat night.
Carlton: Do I make myself clear?

Carlton: Good morning, Geoffrey.
Geoffrey: Playing dress-up again, Master Carlton?
Carlton: For your information, I'm installing the new intercom system.
Geoffrey: You? [laughs]
Carlton: Yuck it up, Brit boy, but remember, he who laughs last... [gets electrocuted]
Geoffrey: Laughs best.

Ashley: Look, Hilary, Derek and I have been spending a lot of time together and we really care about each other. And last night, the subject came up about, um uh, sex.
Hilary: Oh. Oh, did you?
Ashley: No, no. No, heh. But I've been thinking about it and I just wanna know how you know if...
Hilary: I can just tell you that for me, Lawrence and I really loved each other and we both felt that we were able to make a responsible decision. We decided that the time was right.
Ashley: Any regrets?
Hilary: Didn't I tell you he was buff? Hello.
Ashley: But, I mean, Hilary, weren't you scared?
Hilary: Of course, everyone is. But I was ready. And only you know if you're ready or not. Ashley, for as long as I can remember, you have been independent, responsible and smart. Now, I know you're aware of all the issues and whatever decision you do make, I'm always here for you.
Ashley: Thank you, Hilary.
Hilary: Oh. Hoo! Now I know how Mom felt when we had this talk.
Ashley: What did Daddy say when you told him?
Hilary: Are you kidding? He still thinks I'm a virgin.

Will: So, Derek, you know about football?
Derek: Yeah.
Carlton: Yeah, you do? Or, yeah, you don't?
Will: Are you familiar with the term "offsides"?
Derek: Oh, yeah. That's when somebody crosses the line too soon.
Carlton: Exactly.
Will: So I can see you know what I'm talking about here then, bro?
Derek: No.
Carlton: No, you do? Or, no, you don't?
Will: Carlton. Let's put it this way. You're rounding third base and you're headed for home. You're excited because you think you're about to score easy, but here's the problem. You're in a visitor's ballpark and if you do score, the angry fans might not be able to be held responsible for their actions.
Carlton: And it's bat night.
Derek: All right, are you two in trouble with a bookie or something?

Will: I know. I said it was wrong. It's just hard for me to accept the fact that you're doing the... You know, that you're gonna be... you know. I mean, I know you're cute, it's just that...
Ashley: Will, let's just forget about it.
Will: Well, no. No. I can't forget about it. In my eyes, you still the little girl that used to follow me around all the time. Now you wearing dresses and got makeup and the whole nine. It's just... It makes me uncomfortable to know that you're having a, you know, sex life.
Ashley: Fine. Be uncomfortable. [Will sighs] Look, Will I didn't do anything. I mean I love Derek. And I thought I was ready but I'm not.
Will: You know, for a minute, just for a minute I forgot how smart you are. I guess I kind of panicked a little bit.
Ashley: Yeah. You remember the first time I asked you about sex? You panicked then too.
Will: I did not.
Ashley: Yes, you did. You said that you needed to have a license to have sex and that I couldn't even take the test until I was 35.
Will: That's true.
Ashley: Well I guess it's not the worst thing in the world to have a cousin who cares too much.
Will: All right, come here.
Carlton: [over intercom] That was so beautiful.