Dean: After school, you come out and sit under that tree there, and you read. Last week it was Madame Bovary. This week it's Moby Dick.
Rory: But why would you-
Dean: Because you're nice to look at. And because you've got unbelievable concentration.
Rory: What?
Dean: Last Friday, these two guys were tossing around a ball and one guy nailed the other right in the face. I mean, it was a mess. Blood everywhere, the nurse came out the place was in chaos, his girlfriend was freaking out and you just sat there and read. I mean, you never even looked up. I thought, "I've never seen anyone read so intensely before in my entire life. I have to meet that girl."
Rory: Maybe I just didn't look up because I'm unbelievably self-centered.
Dean: Maybe, but I doubt it.

Dean: I gotta place an order.
Jess: Talk into the clown.
Dean: I am.

Dean: Their eating habits are just the start of what you have to get used to. There's tons of stuff you should be aware of.
Max Medina: Really?
Dean: Oh, yeah. Like, don't ever use the last of the Parmesan cheese. And never get into a heavy discussion late at night 'cause that's when they're at their crankiest. And, uh, go with their bits.
Max Medina: Their bits?
Dean: Yes, like if you're eating pizza with them, and Lorelai decides that the pepperoni is angry at the mushrooms because they have an attitude and then she holds up a pepperoni and the pepperoni asks for your opinion... don't just laugh. Answer the pepperoni.
Max Medina: Answer the pepperoni.
Dean: And don't let them near puppies, they'll want every one.
Max Medina: That one I knew.
Dean: Oh, and here's a big one. If you ever think that they're doing something crazy, they're not. You see, after a while, their thinking becomes clear, but by the time it's clear they've done two other crazy things that you can't figure out. So there's no catching up.
Max Medina: You have much knowledge.
Dean: You got that from Rory.

Jess: I'm gonna sit here as long as I like, and I'm gonna do whatever I like, and if you don't like it, then just ignore me and pay attention to your boyfriend.
Dean: Sorry, she can't. I'm not her boyfriend anymore.
Rory: What?
Dean: You know, I tried to ignore this. I really did, but I don't know what the hell I was thinking.
Rory: What are you talking about?
Dean: You don't wanna be with me, Rory.
Rory: Yes, I do.
Dean: Oh, please! You've been into him since he got to town, and I have spent weeks – months, actually – trying to convince myself that it wasn't true, that everything was fine between us. But now I know that I was an idiot. You're into him and he's into you, and Shane, who by the way, should be listening to this 'cause it's so damn obvious.
Rory: What's obvious? What did I do?
Dean: Everyone can see, Rory! Everyone. And I'm tired, but I'm over it, so go ahead, go. Be together. There's nothing standing in your way now, 'cause I'm out.

Dean: What are we watching?
Lorelai: The incomparable Donna Reed Show.
Rory: What's in there?
Dean: A salad.
Rory: Salad?
Dean: Yeah, it's a quaint dish sometimes used to precede large quantities of pizza. [Lorelai and Rory give Dean a puzzled look] It's for me.
Rory: Clearly.

Rory: You're building me a car?
Dean: I'm building you a car.
Rory: This is crazy. Why would you do this?
Dean: I don't know. You didn't have one.
Rory: You're completely insane.
Dean: What? I didn't want you wasting time on the bus anymore. That is valuable time we could be arguing about your ongoing obsession with very confusing Russian authors.

Jess: Give me your order and get out.
Dean: Service with a smile. Six burgers, three cheese two cheddar, one Swiss. Two plain burgers, one chili burger with cheese and onions on the side. Three ham on ryes one mayo, one mustard, one combo. A combo means mustard and...
Jess: I know what a combo means.
Dean: Sorry, guess that confused look is just how your face is.

Rory: It's good, huh?
Dean: It's the Rock and Roll Hall of Fame Induction.
Rory: Yes, and doesn't Neil Young look cool?
Dean: I guess.
Rory: If you'll notice, he's wearing a tux.
Dean: Neil Young looks cool because he's Neil Young, not because he's wearing a tux.

Rory: Dean, this whole friend thing with us isn't going to work if we're not honest with each other.
Dean: I agree.
Rory: Okay, so, anything you wanna tell me?
Dean: Corn's two for a dollar?
Rory: Jess has a black eye.
Dean: Oh, yeah?
Rory: Any idea where he got it?
Dean: That would be an extremely long list.
Rory: It wasn't you?
Dean: It wasn't me.

Luke: Here we are.
Dean: She's smart, man. You know, she's so smart.
Luke: I know, I know.
Dean: She could probably fix the world, you know?
Luke: Right, right. She could team up with Kyle - her brains, his brawn.
Dean: No, not Kyle. Rory.
Luke: Almost there.
Dean: She's the one, you know?
Luke: Come on, Dean, just slide down there, stop talking.
Dean: And the hair, pretty hair. She has the prettiest hair. And that head. What is that?
Luke: Just your shoes.
Dean: I miss her. [sighs] Why didn't she love me?