Will: Look, Jazz, if you want to get with Hilary, man, you got to have a plan.
Jazz: You mean mine hasn't been working?
Will: Jazz, that's the 18th time she threw you out of the house.
Jazz: All a part of my plan.
Philip: [o.s.] We're home.
Jazz: Later.

Ashley: Well, Carlton has sunk to a new low.
Will: What? Carlton, what's up with the crutches?
Carlton: I'm practicing my new scam. Girls love a guy with a sports injury.
Will: Carlton, I can't see too many honeys being impressed by: "Hey, babe, I busted myself up playing peewee football."

Hilary: Mom, Dad, I'm so glad you're home. I have exciting news about my job.
Philip: What is it?
Hilary: Well, I'm not going to just tell you. That's no fun. Guess.
Ashley: Did you sell a painting at the gallery?
Hilary: No.
Philip: Did you get a promotion?
Hilary: No.
Will: Did you get fired?
Hilary: No, I quit.
Phil & Vivian: What?
Will: Yo, I was definitely the closest.

Vivian: Will, please. Hilary's obviously very excited about this job. Be a little more supportive.
Will: You're right. I'm sorry.
Philip: Oh, Hilary, I loved her in that musical she did. God, what a voice.
Will: Lip-synch.

Jazz: Psst.
Will: Jazz, I thought you left.
Jazz: Why?
Will: Because you walked out the door and you said, "Later."
Jazz: All a part of my plan.

Will: Did you hear the news about Hilary?
Jazz: Yeah. I'm so proud of her.
Will: Okay, tomorrow's her first day at work. I think I got a little plan that will make Hilary like you. Tomorrow we'll go down there and you're gonna surprise her with flowers and candy.
Jazz: Cool.
Will: Meet you here tomorrow at 9:00 sharp.
Jazz: You got it, man. Don't forget the candy and flowers.

Hilary: Marissa.
Marissa Redman: Heather.
Hilary: Hilary.
Marissa Redman: Now, let's get one thing straight. My last assistant quit on me because I never learned her name. Now, is that going to be a problem?
Hilary: No, no.
Marissa Redman: Good.
Hilary: I'm so excited. I want to learn all about the movie business.
Marissa Redman: And you will. The key is to be positive. I like positive people. Are you positive?
Hilary: Oh, yes! Yes, yes, yes. Yes.
Marissa Redman: Remember, this is a process. You do realize it's a process?
Hilary: Oh, yes. I'm positive it's a process. [chuckles] [phone rings] Oh, I'll get that.
Marissa Redman: You got that right.

Hilary: [answers phone] Miss Redman's office. I'm afraid Miss Redman's on the other line now, Mr. Haskell... But I'll see if she's finishing up.
Marissa Redman: It's my agent. [takes phone] Hello, Sam. This better be good news. So you're saying I didn't get the part? I know the part called for a Meryl Streep type. And yes, I am a Meryl Streep type if I want to be. It's called acting, Sam. So what fool got the part? Meryl Streep. Ain't that cozy? [hangs up]
Hilary: I'm sorry you didn't get the part, Marissa. But let's be positive. After all, this is a process.
Marissa Redman: Oh, shut up.

Marissa Redman: Now, look, I have to go to a restaurant opening tonight. So I need you to pick up my clothes from the cleaners. Oh, and I'm not speaking to my tired boyfriend, so I'll need someone to go with. I wonder if that cute little Johnny Gill is free.
Hilary: Isn't he, like, my age?
Marissa Redman: Oh, I see. I get it. First, I'm too Black to play Meryl Streep's parts and now I'm too old to date a 20-year-old. Cher can do it, but I can't?
Hilary: No, Marissa, I didn't mean anything like that.
Marissa Redman: Everyone's trying to fit me into their nice, neat little box, aren't they? Well, you're walking a fine line, Helena. A very fine line.

Hilary: [on the phone] Hello, I'm calling from Marissa Redman's office. Is her dry-cleaning ready? It says here on the ticket: "Three dresses, two blouses, four silk brassieres "and eight pair of underwear." Fantastic.
I'll be right over to pick them up.
Will: Glamour, glamour, glamour. You know, Hilary, while you're down there you may even get to see Dustin Hoffman's drawers.