You're sitting on a winning lottery ticket and you're too big of a pussy to cash it in.


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.

Maybe you're perfect right now. Maybe you don't wanna ruin that. I think that's a super philosophy, Will, that way you can go through your entire life without ever having to really know anybody...


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.

So this is a Harvard bar, huh? I thought there'd be equations and shit on the wall.


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.

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


If you ever disrespect my wife again, I will end you. I will fucking end you. You got that, chief?


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.


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.


My boy's wicked smart.


Will: Do you like apples?
Clark: Yeah.
Will: Well, I got her number. How do you like them apples?

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