Hilary: So, Will, dating an older woman. I'm so proud of you. This is just like Cher and that bagel boy.

Vivian: So, Kayla's been spending a lot of time with you.
Will: You know, Aunt Viv, I'm sort of like a big old bag of Lay's potato chips. It's like, once you get a taste, you just can't stop.
Philip: Well, you're certainly like a big old bag of something.

Ashley: Are you guys just gonna watch TV all day?
Will: Come on, Ashley, this is for school.
Man: [on TV] And our spokesmodeI winner is Randy!
Will: Yes! I knew she was going to win.
Ashley: Look, I know you two haven't had dates in a while but how desperate can you get?
Will: Well, I know how desperate I can get. How about you, Carlton?
Carlton: Sky's the limit.
Ashley: I better go lock up my Barbies.

Will: I don't know, Carlton, man. It sure has been a long time since I had a girl.
Carlton: Tell me about it. Last Friday, the school nurse started looking good to me.
Will: Yeah, man, something about how them fat ankles roll over them squeaky white shoes.

Geoffrey: Dinner is served.
Philip: Thank you, Geoffrey.
Kayla: So, uh, who's that English dude?
Will: Oh, Geoffrey? Yeah, he's down with my posse. You know, he cuts a nice fade, so I keep him around.
Kayla: Well, don't that make you large.

Carlton: Will, what are you trying to do?
Will: When you grow up, Carlton, we'll have to have that little talk.
Carlton: Don't make me laugh. You won't reach first base with her. To borrow a phrase from your street lingo she just hits you with a pretty hard disk.
Will: The word is "diss."
Carlton: I don't care whether it's diss, dat, or the other thing. Will, she goes to college. She's not a girl, she's a woman. They don't go out with high school boys.
Will: Look, maybe not out here, but Kayla and I are both straight out the 'hood, man. Where we come from, age don't make no difference. 17, 21, 33, they're all in the same grade.

Vivian: Come on. We got to find those car keys. Kayla's coming any minute. I promised her I'll take her to a poetry reading at USC and I don't wanna be late.
Will: No, hold on. Wait. Kayla's coming over here? Look, I'm out of here. I don't even want to hear that girl's name.
Vivian: Fine, Will. We don't have to talk about her.
Will: Good. You know what my beef with Kayla is?
Philip: Will, I thought you didn't want to talk about Kayla? [doorbell rings]
Vivian: There's Kayla.
Will: Great. This is great. I'm out of here. I'm leaving. [sits down on couch]

Geoffrey: Miss Kayla Samuels.
Vivian: We'll leave as soon as we find the car keys.
Ashley: Mom, maybe we should just drive around town and look for Hilary's keys.

Will: Man, how come you didn't want to go?
Kayla: I've been to one of those parties, Will. It's like being on the moon or something. I had nobody to talk to and I just left after 10 minutes.
Will: Well, that's all right. Here, come on. We can go to a party at my fraternity.
Kayla: Your fraternity?
Will: Yeah, Sigma Fly.

Will: When you've got a fantastic woman at your side, you feel like a million bucks.
Carlton: I've got a splitting headache.
Will: Carlton, you know, when I have a headache Kayla breaks out the baby oil and gives me one of them strong back rub. Then right after that...
Carlton: Oh, I don't want to hear about this. I'm going to school.
Philip: It doesn't start for an hour.
Carlton: I know, but sometimes there's a girls' volleyball game in the gym and they wear those little shorts, and... That's really pitiful, isn't it?