Lorelai: I hate crossword puzzles. They make me feel stupid.
Rory: Then don't do them.
Lorelai: No, but if you don't, you're not only stupid you're also a coward.
Rory: Or you have better things to do with your time.
Lorelai: You think people will buy that?
Rory: The people who line up on a daily basis and ask if you do crossword puzzles and then when you say no, challenge you as to why? Yes, I think they will buy it.

Rory: They're not going to fire Dean.
Lorelai: Why not?
Rory: For starters, someone stole Taylor's ladder last week and Dean is the only one who can reach the top shelves.
Lorelai: Interesting.
Rory: What?
Lorelai: Just as Marty, a.k.a. Eve Harrington, shows up trying to take Dean's job Taylor's ladder mysteriously disappears suddenly making Dean invaluable no matter what fancy tricks Lon Chaney Jr. over there pulls. Good thinking, Dean. Smart thinking, my friend.
Rory: You need to start napping in the afternoons.

Luke: What's he done?
Principal Merton: Why do you think he's done something?
Luke: You're staring at a folder that's looking a little thick there I get a call to come over and talk to you. So why don't you just tell me what he's done?
Principal Merton: Nothing.
Luke: Nothing?
Principal Merton: No homework, no class participation. His attendance record is erratic at best. His attitude to his teachers ranges from indifferent to hostile. He shows no interest in activities or other students and there is the issue of the disappearing baseballs.
Luke: The what?
Principal Merton: Every baseball on campus seems to have disappeared.
Luke: And you don't think Jess seriously- [Principal Merton looks at Luke] I'll check when I get home.

Principal Merton: You have to help him.
Luke: Me? No, I'm not the one you want helping him. I went to this school. I'm sure there's still a note stuffed in there about me with the words 'Trade SchooI' stamped in really big letters.
Principal Merton: If you can't help, you have to find someone who can.
Luke: Like who?
Principal Merton: A relative.
Luke: I don't think so. Believe me, I'm the Einstein of the clan.

Lorelai: So, do you want to get some pie?
Rory: No, I'm full.
Lorelai: Coffee? How about some coffee?
Rory: I'm good.
Lorelai: Hot chocolate?
Rory: No, thanks.
Lorelai: Egg cream? Now, I've never had an egg cream, but it sounds just disgusting enough to be fabulous.

Rory: Are you ready to start?
Jess: Yes, I am.
Rory: Where are your books?
Jess: I don't know.
Rory: How are we going to study?
Jess: Huh. I guess we can't. Too bad. So, what now? Movie?
Rory: Get your books.
Jess: The cat ate them.
Rory: Get your books or I'm going home.

Rory: So, if we go get ice cream-
Jess: In cones.
Rory: Then you'll be a perfect student for the rest of the night?
Jess: That's right.
Rory: I could not believe you less. Here. You drive. I'll read you Othello. Won't that be fun?
Jess: You have no idea how much.

Rory: Do not give me that whole "I'm so misunderstood", Kurt Cobain-y thing. You are way stronger than that, and I don't even want to hear it. You have to go to college.
Jess: No, you have to go to college.
Rory: Don't you have any plans?
Jess: I plan to get out of Stars Hollow.
Rory: And go where?
Jess: Wherever.
Rory: And do what?
Jess: Whatever.
Rory: "Whenever. Whatever."
Jess: I'll live where I live, I'll work when I need money and I'll see where I end up.
Rory: You could do more.
Jess: Oh, here come the pompons.
Rory: No. No pompons. Just me saying, "You could do more."

Lorelai: So they brought you in the ambulance?
Rory: Yeah.
Lorelai: Did they use the siren?
Rory: Yeah.
Lorelai: I hope Taylor was in bed.
Rory: It was after 9:00, so there's a good chance.
Lorelai: Nice.

Rory: Mom, you don't have to sleep in here tonight.
Lorelai: I think the chair looks nice here.
Rory: What's the blanket for?
Lorelai: In case the chair gets cold.
Rory: The pillow?
Lorelai: To keep the blanket company. Okay, everything's in its place. Chair seems warm, blanket seems happy. Just one thing missing. Oh... [sits down] Good night.
Rory: Freak of sideshow proportions.
Lorelai: I love you, too.
Rory: Mom. I'm sorry.
Lorelai: Ssh. The chair is trying to sleep.