Dean: It's not working with Lindsay. I can't make it work. I've tried.
Rory: Are you sure? Because I've heard that the first two years of marriage are the hardest.
Dean: We're not happy. She's not happy, and I can't make her happy.
Rory: I can't imagine that.
Dean: It was a mistake, and I know that now. From the very beginning, it wasn't-
Rory: Wasn't what?
Dean: It wasn't...
Rory: Maybe you could, um, go see a counselor or go away together.
Dean: No, it's just... It's over. We both feel it. I know we both feel it.

Rory: You and Lindsay?
Dean: Yeah, me and Lindsay.
Rory: You both feel it's over?
Dean: I tried. We tried.
Rory: Well, if it's over, I'm sorry.
Dean: You are?
Rory: I'm sorry you're not happy.
Dean: I'll be happy again. Things happen for a reason, right?
Rory: Right. I can't believe this is that we're...
Dean: I can. [they kiss]

Dean: Did I ever tell you I like your hair?
Rory: My hair?
Dean: Your shorter hair.
Rory: It's grown out a little.
Dean: I like it.
Rory: I like it, too.
Dean: So, um, you wanted to talk?
Rory: Yeah, talk. Words... wow. [they kiss]

Lorelai: It's a letter for you from Rory.
Dean: What happened? Where is she?
Lorelai: Just take the letter.
Dean: She went to Europe, right? Miss Patty said she went to Europe. What happened? What's she doing there? Who is she with?
Lorelai: Dean.
Dean: When's she getting back?
Lorelai: Soon. Just take it.
Dean: Where is she?
Lorelai: Europe.
Dean: With who?
Lorelai: Her grandmother. Look, take it.
Dean: No. Why did she go? I mean, whose idea was it?
Lorelai: That doesn't matter.
Dean: It does.
Lorelai: Dean, please. I'm a messenger, nothing more. Just take it.

Dean: Um, let's see. How do I feel? Actually I feel like an idiot.
Rory: Why?
Dean: Why? Because I was married, Rory. Married. And I threw it all away for someone who dumped me once and then just bailed on me.
Rory: I didn't just bail.
Dean: I- I hurt everybody. I hurt Lindsay, I hurt her parents, I hurt my parents, and now I'm back at home, and you're in Europe with your grandmother. And what the hell was I thinking? I mean, what am I doing? What's wrong with me?
Rory: Nothing.
Dean: I got to get ready for work.

Dean: Because your stuff is good and has to be eaten pretty quickly. If it sits around, it starts to suck.
Luke: That's true of all food.
Dean: Ah, but not Jojo's. Jojo's sucks to begin with, so it's no worse when you eat it later.
Rory: It's a relativity thing. Einstein and whatnot.
Lorelai: The secret is Jojo's chili. The chili acts as a seal.
Rory: Jojo's burgers could travel to China, and they'd still be just as good.
Dean: Because they start off bad.
Lorelai: Get it?
Luke: Not really.

Rory: [on the phone] Since when do you work on Thursday?
Dean: Since Taylor decided to cash in on the 24-hour trucker crowd.
Rory: What trucker crowd?
Dean: The trucker crowd off Highway 84.
Rory: Since when does the trucker crowd off Highway 84 come through Star's Hollow?
Dean: Since we installed an Icee machine.

Dean: What am I doing here, Rory?
Rory: You're picking me up.
Dean: I don't belong here. Not anymore. Do I?
Rory: Dean.
Dean: You look good. [drives off]
Logan: You'll be okay.
Rory: No, I won't.

Dean: They want more than this. Don't you see that? And all you are is this.
Luke: Rory was a kid, Dean. She grew up. She moved on. Accept it.
Dean: You accept it. This town, it's all you are, and it's not enough. She's going to get bored, and you can't take her anywhere. You're here forever.
Luke: It's different.
Dean: It's not different. You and me. Same thing.