Max Medina: How about you?
Lorelai: I've never been married.
Max Medina: Ever been close?
Lorelai: Rory's dad proposed.
Max Medina: What happened?
Lorelai: The bell rang. I was late for chem lab.
Max Medina: You ever sorry that you didn't?
Lorelai: Oh, no, we were so young and my life would've been completely different. You know, I wouldn't live here. I wouldn't work here. I wouldn't be walking here with you.

Max Medina: Where are we going?
Lorelai: You'll see.
Max Medina: Are we gonna get there before we freeze?
Lorelai: What kind of fun would it be if I told you the answer?
Max Medina: You're crazy.
Lorelai: Very possible.
Max Medina: And I'm following you.
Lorelai: Yes, you are.
Max Medina: So possibly I'm crazier then you are.
Lorelai: Again, very possible.
Max Medina: A match made in heaven.
Lorelai: Or in Bellevue.
Max Medina: It must be fate.

Richard: [on the phone] This is getting ridiculous, Aaron. I will not continue to have these conversations with a child. Yes, he is a child. When he's worked 30 years at the company, he won't be a child. Well, until then, I don't care what his opinions are. Aaron, are you listening to me? Good, because I'm hanging up on you now and I wanted to make sure that you heard it. [hangs up] What a moron.

Emily: Ah, look at this.
Rory: That's one fluffy white dress.
Emily: Yes, there were 12 petticoats underneath it. We got it in London, remember, Richard?
Rory: She looks like a little princess.
Emily: Yes, well, if memory serves, I believe about two minutes after that picture was taken Her Highness dumped a glass of grape juice over it.

Emily: Richard, every young girl thinks about her wedding. I know I did. I knew from the time I was 12 that I wanted lilies and orchids with a silver bow wrapped around them for my bouquet.
Richard: You also knew that you wanted to marry Errol Flynn.
Rory: Really, Grandma had a thing for the pirate guy?
Emily: I did not have a thing for the pirate guy.
Richard: She was mad about him. She even tried to get me to grow one of those mustaches.
Rory: You're kidding.
Emily: Richard, stop.
Richard: She wanted me to swing from a chandelier.
Emily: Now you're just being silly.
Richard: Luckily, I was on the fencing team at college or I would have married Lucinda Lester by now.
Emily: Actually, Lucinda Lester looked a lot like Errol Flynn. [Richard chuckles] I should have married her. It would have been very modern of me.

Rory: Wow. Mom looks really beautiful here.
Emily: Yes, she does.
Rory: What was the occasion?
Richard: Who would like some coffee?
Emily: That was her debutante gown for her coming-out party.
Rory: Mom had a coming-out party?
Richard: No, she didn't.
Rory: Oh.
Emily: Yes, well, things happen, don't they?
Richard: If you'll excuse me, I have some business calls to make.
Emily: I'll go get that coffee.

Lorelai: See, I have really strict rules about dating. I keep my personal life totally separate from my life with Rory. You know, I never want her to feel unsettled or like her life could just shift at any moment.
Max Medina: I totally understand.
Lorelai: And she comes first, and this her house, too.
Max Medina: I understand. This is something that you don't do often.
Lorelai: Ever.
Max Medina: Ever?
Lorelai: Never.
Max Medina: I see.
Lorelai: I mean, I've dated. And, you know, dated. [chuckles] But I've just never dated here, in our house.

Lane: God, I'm so humiliated. I can't ever go back to school. I'll have to be home-schooled. My mother finally gets her way.
Lorelai: Look at it from a different perspective. You have so many years of screw-ups ahead of you. View this as a trial run for really grown-up humiliation.
Lane: So not helping.
Lorelai: Maybe you should be a hairdresser.
Lane: Lorelai.
Lorelai: Yes, it's perfect. Then you can run your hands through anybody's hair and they'll pay you for it.
Lane: What am I going to do? Everyone at school's gonna be talking about me. I can't show my face.
Lorelai: Everybody does stupid things in high school. It's, like, a requirement.
Lane: Not like this.
Lorelai: No, some people get pregnant. Talk about something really juicy for the gossip mill.
Lane: I forgot about that.
Lorelai: Yeah. Everybody screws up, Lane. That's what happens. It's what you do with the screw-ups. It's how you handle the experience. That's what you should judge yourself by. I have a great life and an amazing kid. And I took a detour. I ended up someplace good.

Lorelai: Tell me this. How did his hair feel? Good as it looked?
Lane: Better.
Lorelai: Oh, you're gonna be fine. I'm positive about that.
Lane: Thank you.
Lorelai: You're welcome.
Lane: So who's the guy?
Lorelai: Rory's teacher.
Lane: He has nice hair.
Lorelai: Yeah.

Max Medina: Everything okay in there?
Lorelai: It will be. [sighs]
Max Medina: So, where did we leave off?
Lorelai: Uh, Lane is gonna stay here tonight. She had a really bad teen day and she needs to crash someplace sympathetic.
Max Medina: Okay, I understand.
Lorelai: [sighs] I swear to God, if this wasn't a major Judy Blume moment I would kick her cute little butt right out of here.