Philip: Look, what I'm trying to say is that maybe you've served the community long enough and as your friend, I think I should tell you that well, maybe it's time for you to retire.
Judge Robertson: Me, retire? Oh, Frank. Have you lost your mind? I mean, this is the cushiest job in town. I get free coffee, validated parking I don't have to wear pants, and besides, there's no one to run against me.
Philip: Yes, there is.
Judge Robertson: Who?
Philip: Me.
Judge Robertson: You! You've got to be kidding. You don't know the first thing about running for office. I taught you about law, not politics.
Philip: Look, the point is I'm going to run against you, and I thought I should tell you face to face.
Judge Robertson: Oh, yes? Well, let me tell you something face to face. [stands on a futon] I am a very worthy opponent. And I can see myself in your head. [laughs] Benson, my car.

Will: Judge? Hey, what's going on? What are you doing here?
Judge Robertson: I don't know, don't I live here?
Will: No, Judge, you don't.
Judge Robertson: Ah. [laughs] No wonder the garage door opener didn't work. It took forever to pry it open.
Will: Look, I got some problems, you know, I got to deal with tonight. Woman problems.
Judge Robertson: Ah, women. They've been a problem ever since they got the right to vote. Sit down, son, sit down. Talk to me, sonny, talk to me. I've had my share of problems with women.
Will: Actually, Judge, it's this girl at school, Lindsey, right? She just keep buying me all these fly gifts.
Judge Robertson: So what's the problem?
Will: Well, I'm not really attracted to her.
Judge Robertson: So what's the problem?

Will: Well, my Aunt Viv told me that, you know it's not right to accept gifts from people that, you know, you're not really attracted to.
Judge Robertson: Look, son I remember when I was your age, there was this girl... I didn't like her that much she was always buying me gifts, dinner, taking me out. Heck, she even offered to send me through law school.
Will: So what did you do?
Judge Robertson: What else? I married her. Pie?
Will: No. No, thanks, Judge. So, wait, you're just going to tell me that you got together with this girl, and you had this long, incredible, wonderful life.
Judge Robertson: I wish I could tell you that. But the truth is, I dumped her after law school.
Will: I'm sorry, Judge, that's too bad.
Judge Robertson: Oh, no, it's okay. We split everything down the middle. I got the money, the house, the car, the boat, and she got to keep the kids. Pie?
Will: No. No, thanks.
Judge Robertson: So you're saying that you just kept all this stuff that she gave you, even after y'all broke up? Damn straight. Possession is nine-tenths of the law, my boy.

Judge Robertson: Princess Leia! May the force be with you. [laughs]
Lindsey: Will, somebody broke into your garage.
Judge Robertson: Quick, call the police.
Will: Lindsey, can I talk to you for a second? Look, what are you doing here? [to the judge] As if I didn't know, right?
Lindsey: It's over, Will.
Will: See what I'm saying? It's what?
Judge Robertson: Over.
Will: But why?
Judge Robertson: Why ask why? Look at her.

Lindsey: I'm not attracted to you, Will.
Will: Whoa, whoa, whoa. Yeah. Yes, you are.
Lindsey: No. No, I'm not. I've never been attracted to you.
Will: Well then why did you buy me all this stuff?
Lindsey: Well, you're captain of the basketball team you're popular, and being seen with you at the autumn dance made me popular, too. But now your job is done.
Judge Robertson: Uh, uh, uh. That woman is ruthless. You ever think about going into politics?
Lindsey: Yeah. As a matter of fact, I...

Will: Whoa, whoa, whoa. I'm saying, Lindsey, I mean, what about me as a person? What about the way that my cheeks dimple when I smile? And what color are my eyes? Look at you all quiet. You don't even know.
Lindsey: Who cares?
Will: Who cares? I feel so used, so cheap.
Lindsey: You certainly weren't cheap. Cost me a fortune. I want my stuff back. Now.
Will: Wait. But-
Lindsey: Now!
Will: You take this ring back, 'cause my mother don't scream at me like that. Watch back, and you can take this jacket back.
Judge Robertson: Be sure to rock the vote.
Lindsey: Good night.
Will: You know, Judge I never thought saying goodbye would be so hard. I really loved that watch.