Here is a list of my favorite lines from the movie. I just hope that I can get them all down right.
Skylar: What if I said I wouldn't have sex with you again till I got to meet your friends, what would you say?
Will: It's four-thirty, they're probably still awake.
Chuckie: I didn't get on Cathy last night.
Will Hunting: No?
Chuckie: Nah.
Will Hunting: Why not?
Chuckie: I don't know. [yells across room] Cathy!
Cathy: What?
Chuckie: Why didn't you give me none of that nasty little hoochie-woochie you usually throw at me?
Cathy: Oh, fuck you and your Irish curse, Chuckie. Like I'd waste my energy spreading my legs for that Tootsie Roll dick? So go home and give it a tug yourself.
Will Hunting: Do you like apples?
Clark: Yeah.
Will Hunting: Well, I got her number. How do you like them apples?
Billy: You're 21, you can legally drink. We figured we'd get you a car.
Chuckie: 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.
Sean: If you ever disrespect my wife again, I will end you. I will fucking end you. You got that, chief?
Will: Time's up.
Sean: Nail them while they're vulnerable, that's my motto. See you Monday. We'll be talking about Freud and why he did enough cocaine to kill a small horse.
Skylar: You were hoping for a goodnight kiss.
Will: No, you know. I'll tell ya, I was hoping for a goodnight lay, but I'll settle for like a kiss.
Skylar: How very noble of you.
Will: Thank you.
Chuckie: But you know what the best part of my day is? The ten seconds before I knock on your door, 'cause I let myself think I might get there, and you'd be gone. I'd knock on the door and you wouldn't be there. You just left. Now I don't know much, but I know that.
Chuckie: So this is a Harvard bar, huh? I thought there'd be equations and shit on the wall.
Morgan: Man, I can't believe you brought Skylar here when we're all bombed and drunk. What 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.
Skylar: [laughs] Okay, sounds good.
Skylar: You men are shameful. If you're not thinking with your weiner then you're acting directly on its behalf.
Sean McGuire: The reason he hangs around with those "gorillas," as you called them, is because anyone of those "gorillas" would take a baseball bat to your head anyday. It's called loyalty.
Sean McGuire: If you're gonna jerk off, why don't you just do it at home with a moist towel?
Will Hunting: You wasted $150,000 on an education you coulda got for $1.50 in late fees at the public library.
Will: Why shouldn't I work for the N.S.A.? That's a tough one, but I'll give it a shot. Say I'm working at N.S.A. Somebody puts a code on my desk, something nobody else can break. So I take a shot at it and maybe I break it. And I'm real happy with myself, 'cause I did my job well. But maybe that code was the location of some rebel army in North Africa or the Middle East. Once they have that location, they bomb the village where the rebels were hiding and fifteen hundred people I never had a problem with get killed. Now the politicians are sayin', "Send in the marines to secure the area" 'cause they don't give a shit. It won't be their kid over there, gettin' shot. Just like it wasn't them when their number was called, 'cause they were pullin' a tour in the National Guard. It'll be some guy from Southie takin' shrapnel in the ass. And he comes home to find that the plant he used to work at got exported to the country he just got back from. And the guy who put the shrapnel in his ass got his old job, 'cause he'll work for fifteen cents a day and no bathroom breaks. Meanwhile my buddy from Southie realizes the only reason he was over there was so we could install a government that would sell us oil at a good price. And of course the oil companies used the skirmish to scare up oil prices so they could turn a quick buck. A cute little ancillary benefit for them but it ain't helping my buddy at two-fifty a gallon. And naturally they're takin' their sweet time bringin' the oil back, and maybe even took the liberty of hiring an alcoholic skipper who likes to drink martinis and play slalom with the icebergs, and it ain't too long 'til he hits one, spills the oil and kills all the sea life in the North Atlantic. So my buddy's out of work and he can't afford to drive, so he's got to walk to the job interviews, which sucks 'cause the schrapnel in his ass is givin' him chronic hemorroids. And meanwhile he's starvin' 'cause every time he tries to get a bite to eat the only blue plate special they're servin' is North Atlantic scrod with Quaker State. So what do I think? I'm holdin' out for somethin' better. Why not just shoot my buddy, take his job and give it to his sworn enemy, hike up gas prices, bomb a village, club a baby seal, hit the hash pipe and join the National Guard? I could be elected president.
Sean: She is not perfect. You are not perfect. The question is whether or not you are perfect for each other.