Trix: I've been thinking about something I heard.
Lorelai: What?
Trix: That you borrowed money from your parents for Rory's school.
Lorelai: Well, if you're worried about them getting the money back...
Trix: You know, Shakespeare once wrote, "Neither a borrower nor a lender be." Do you consider Shakespeare a wise man?
Lorelai: Sure.

Lorelai: Gran, I don't know what to say. That's so generous of you.
Richard: My mother is a very special woman, isn't she?
Trix: You talk about me like I'm dead.
Richard: Oh, you're never going to die. You're too stubborn.

Emily: You're not honestly considering accepting that money, are you?
Lorelai: Yeah, of course I'm considering it.
Emily: I don't think that's very wise.
Lorelai: Why not?
Emily: Because she's a young girl. She won't know the first thing about managing that money.
Lorelai: Yeah, well, I'll help her.
Emily: Well, you don't know the first thing about managing that money either.
Lorelai: No, but I'm very familiar with the second thing.

Emily: How come you can't you see the pitfalls involved in accepting this money? I mean, you're the one who brags about how special your relationship with Rory is.
Lorelai: Mom.
Emily: I'm stunned that you want to jeopardize it like this.
Lorelai: What are you talking about?
Emily: Well, you know as well as I do that money means freedom.
Lorelai: And?
Emily: If Rory has that money she won't need you anymore.
Lorelai: [scoffs] I don't know, Mom, she's 16. There's still some ways I may come in handy. You know, buying beer and that kind of stuff.
Emily: Well, I'm glad you think losing your daughter is so funny.

Emily: She'll be self-sufficient. She won't need you to pay for anything, she won't have to turn to you.
Lorelai: Everything in a relationship isn't about money, Mom.
Emily: She'll move out as soon as she can.
Lorelai: So what?
Emily: She won't need you to help her with her college. She won't need you to buy her a car.
Lorelai: Okay, you know what? Say goodbye to Dad for me as soon as the voices in your head subside.
Emily: Why should she wait to backpack across Europe with you? She can afford to go herself, and she can take a friend or a boyfriend or anyone.
Lorelai: Yeah, well, she wants to go with me.
Emily: Well, now she does. She doesn't have options. But the minute you give her options...
Lorelai: Okay, that's it. You're nuts, and I'm going. In that order.
Emily: It's terrible not to be needed. You'll see.

Sookie: That is amazing!
Lorelai: I know. One minute it's, "Pass the pot roast." Then it's, "Have a pile of money." Things are never boring at the Gilmore house.

Sookie: What did Rory say?
Lorelai: I haven't told her yet.
Sookie: What?
Lorelai: She was asleep when I got home.
Sookie: For that much money, you wake her up. You hire singing telegrams, women jump out of cakes. People dressed up like bankers and dance around with those toasters.
Lorelai: She's been working her butt off all week on this Chilton paper so I let her sleep. I'll tell her tonight.
Sookie: Call her now. Ooh, or page her and have her call me and we can sing The Money Song from Cabaret. You be Liza, I'll be Joel.
Lorelai: I don't know.
Sookie: Okay, I'm Joel.

Sookie: Lorelai, come on, this is Rory we're talking about.
Lorelai: I know.
Sookie: She's the most unmaterialistic kid in the world.
Lorelai: No, it's not about what she would buy. I don't care if she buys a house, or a boat, or the Elephant Man's bones. It's just that... You know, it's about the freedom. If I had access to all that money as a kid I would've left the house so fast.
Sookie: Faster than 17?
Lorelai: No, I mean... God, I know this is crazy. I have my mom's voice stuck in my head. It's like that annoying Cranberries song. I hate that I let her do this. I hate that I let her get to me.

Lorelai: I've got to go home.
Sookie: Why? What are you doing?
Lorelai: I have to change and go to tea with Gran and the cast of Gaslight.

Rory: What?
Paris: It was your idea?
Rory: Paris.
Paris: So, what, I get all your castoffs now? I'm just that pathetic? "Gee, I don't want them, so maybe I can con the suckers into taking out Paris the loser! Throw the dog a bone!"
Rory: Okay, let's-
Paris: I am not your charity case!
Rory: No, it's not like that, I swear. I just thought you guys would make a good couple, that's all.
Paris: We did, for one night. But apparently we're more suited to being friends. At least, that's what was conveyed so humiliatingly to me five seconds ago.
Rory: Paris, I'm sorry.
Paris: I hate you.