Will: Hilary. Listen. That is not a mole or an Adam's apple that you're seeing. It's Trevor.
Hilary: You're telling me that Trevor was reincarnated in Scott's throat?
Will: No, look, Hil, what I'm trying to say is that you miss Trevor so much something inside of you won't let go of him. If you walk out on Scott now, this could haunt you for the rest of your life.
Hilary: What do you mean?
Will: Well... You might never go out again. You'll become one of them crazy old women who walk around all day long with a shower cap on, with an old raggedy halter-top that say "Jam." And then you gonna start wearing rhinestone gauchos. And then, just for no reason, you'll say: "Dum-dum-diday" Then you'll be eating neckbone sandwiches all the time. And screaming at your little imaginary dog, Brutus. And you know what the worst part is?
Hilary: What?
Will: The only man you're gonna be able to get is some fool named Grady, who be smelling like menthol all the time and falling asleep in his soup.
Hilary: Oh, God, I hate soup.
Will: Then you march through those curtains and you look his throat in the face!

Vivian: Philip, the important thing is that you and your son spent quality time together. You should be proud of what you built.
Geoffrey: Even if it is a deathtrap.
Philip: You are just jealous because you don't have son like Carlton to build something with.
Geoffrey: Yes, sir, that must be it. Look! It's a bird. It's a plane. It's Master Nicky.

Vivian: Here, darling. Philip, I know what's gonna happen. Carlton's gonna start in on your nerves and you're gonna end up at his throat.
Philip: Oh, nonsense. This is a perfect time for a father and son to spend some quality time together. Geoffrey, go fetch my tools.
Geoffrey: You mean your knife and fork?

Will: What is the matter with you? You are making a mountain out of a mole, Hil.

Will: Hey, Hil, you got a second?
Hilary: Sure.
Will: All right. Sweet Savage Lust. One of the classics, huh?
Hilary: It's about this rich, beautiful girl who loses her lover in a terrible accident and spends her nights alone mourning his death. Where do they get these stories?
Will: Hey, look, Hil you know, Trevor's been gone for months now. Don't you miss dating?
Hilary: Yeah. At first, I felt guilty for wanting to. But I think if Trevor were still alive, he'd want me to see other guys.

Will: Hilary. Tonight, I hurt somebody that I really care about.
Hilary: What about me, Will?
Will: I meant you.
Hilary: Oh. Thank you. But you were right.
Will: I was?
Hilary: Scott is the first guy since Trevor that I really liked. And I guess I got scared and I had to find something wrong with him.
Will: And that Adam's-apple thing was the best you could do, huh?
Hilary: Well, I never had much of an imagination. When I was a little girl, I never had any imaginary friends. I just used to play with Carlton's. And, God, they were such dweebs.

Philip: Hey, everybody. I just bought Nicky a brand new crib.
Carlton: "The Crib Chalet has over 100 features including automatic guardrail-extension, infrared climb-out sensors and a built-in busy box. Some assembly required." Oh, no.
Philip: Carlton, my boy, go put on your work clothes.
Carlton: [to Vivian] Help me.
Ashley: I'm not gonna miss a minute of this.

Will: All right. Hey, you know what? Allow me. "Will, you should be ashamed of yourself." "Hey, Jackie, I can explain." "Explain what? How you're using your cousin just to get yourself a good grade?" "Hey, look, Jackie, it ain't like that." "I know you, Will. But I still burn with desire for you, baby."
Jackie: "Yo, Jackie. I'm just looking out for number one. You know what I'm saying? You know, you know."

Will: Hilary, listen. Imperfections are what make people special. Like in Philly, a big butt on a sister was considered a thing of beauty. You know, the more back baby got, the better. I mean, up to a point. Then, it's just nasty.

Carlton: Dad, we started this three days ago and there's no end in sight. Let's pay someone to finish the job.
Philip: Am I keeping you from something more important?
Carlton: As a matter of fact, yes. I've got midterms and, eventually, I'd like to move out get a full-time job and start a family.
Philip: And when you do, I will help you build one of these for your child.
Carlton: No, you won't, because I'll be smart enough to pay someone to do it for me.
Philip: And just how are you gonna do that without a trust fund?
Geoffrey: Game, set, match.