Look, you're my best friend, so don't take this the wrong way. In twenty years, if you're still livin' here, comin' over to my house to watch the Patriots games, still workin' construction, I'll fuckin' kill you. That's not a threat. Now, that's a fact. I'll fuckin' kill you.

Chuckie

I can be in the NBA. I'm tall, I like to wear shorts. Hook! Hook! Dunk! Dunk! Baby, I'm all about three points.

Skylar

See you Monday. We'll be talking about Freud and why he did enough cocaine to kill a small horse.

Sean

Skylar: You were hoping for a goodnight kiss.
Will: No, you know. I'll tell ya, I was hoping for a goodnight laid, but I'd settle for a good night kiss.
Skylar: [Bursts out laughing] How very noble of you.
Will: Thank you. But I was, you know, hoping for a good night kiss.

Morgan: Man, I can't believe you brought Skylar here when we're all fucking bombed and been drinking. What the fuck is she gonna think about us?
Will: Yeah, Morgan, it's a real rarity that we'd be out drinking.

Skylar: Maybe we could go out for coffee sometime?
Will: Great, or maybe we could go somewhere and just eat a bunch of caramels.
Skylar: What?
Will: When you think about it, it's just as arbitrary as drinking coffee.

Will: No, not a lick. I mean, I look at a piano, I see a bunch of keys, three pedals, and a box of wood. But Beethoven, Mozart, they saw it, they could just play. I couldn't paint you a picture, I probably can't hit the ball out of Fenway, and I can't play the piano.
Skylar: But you can do my o-chem paper in under an hour.
Will: Right. Well, I mean when it came to stuff like that... I could always just play.

Will: Does this violate the doctor-patient relationship?
Sean: Not unless you grab my ass.

Chuckie: Morgan, I'm not going to Kelly's just because you like the take out girl. It's fifteen minutes out of our way.
Morgan: What the fuck are we gonna do that we can't spare fifteen minutes.

What am I, fuckin' sandwich welfare? I think you should establish a good line of credit. Like how you bought your couch, payment plans. Remember how your mother brought in $10 everyday for a year and she finally got her couch Rent-A-Center Style?

Chuckie

Lambeau: Yeah, you were smarter than me then, and you're smarter than me now. So, don't blame me for how your life turned out.
Sean: I don't blame you! It's not about you, you mathematical dick! It's about the boy! He's a good kid! And I won't see you fuck him up like you're trying to fuck up me right now! I won't let you make feel like a failure too!

I just have a little question here. You could be a janitor anywhere. Why did work at the most prestigious technical college in the whole fuckin' world? And why did you sneak around at night and finish other people's formulas that only one or two people in the world could do and then lie about it? 'Cause I don't see a lot of honor in that, Will.

Sean

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