Bailey: I'm such a moron. I can't believe what a moron I am.
Will: You are a moron.
Bailey: I...I just, kinda forced the issue.
Will: The issue?
Bailey: With Kate about Tom.
Will: The boyfriend?
Bailey: Yep.
Will: You said him or you?
Bailey: Pretty much.
Will: Wow
Bailey: Yeah
Will: And?
Bailey: And what? Would I be a moron if everything would have worked out?
Will: Good point by you.

Bailey: Is this like some kind of big emergency, Claud?
Claudia: Well....kind of, yeah. The thing is...I just got my period.
Bailey: Oh...

Bailey: Okay so I hire 2 big guys to kidnap him and take him off to some remote island or Hawaii, someplace. Just so Kate doesn't see him for a while and then eventually she forgets all about him.
Will: Hmm. I don't know Bay. Kidnapping? I don't think they let you graduate from high school if you've kidnapped somebody.

Bailey: There's no way you can do this, Charlie, ok? You can't! So you go. You go, and you do what you have to do. We're not going with you.
Claudia: We're gonna get split up.
Bailey: That's right. That's right. I hope you can live with that, Charlie.

Charlie: [in response to the party Claudia threw at the house] I thought I said...
Claudia: You said I was grounded, that I couldn't go out. Well, I didn't go out. I brought everyone in.

Charlie: [to Claudia] Are you afraid of having an accident or something?
Bailey: She's afraid of spilling.
Julia: Staining.
Claudia: Oh God, I'm going to die.

Charlie: For God's sake, Claud, I don't have time for this! You think you're gonna miss school every time you get your period?
Claudia: I just don't feel like going! I'm moody.
Charlie: You're moody all the time.
Julia: Problem?
Charlie: Claudia's not going to school, she got her period.
Julia: So? It's her first time. She's nervous.
Claudia: I'm not nervous! I just don't feel like going!
Bailey: What's going on?
Charlie: Claudia's period.
Claudia: Why don't you just invite the neighbors over, and we can all talk about it!

Charlie: I don't know, Bay. Maybe the thing to do is look for people who actually want your help and just help them.

Charlie: I mean, writing things down, it just comes so naturally to you. You're a real good writer, Jul. And I know I'm not the best advice-giver or anything, but...I think whatever you do, you shouldn't stop writing. Whatever you do, you should write about it.

Charlie: I really need your help. What do you say?
Claudia: Sorry. Too risky.
Charlie: [to Julia and Bailey] You know, you just can't buy love like that.

Charlie: Julia get down here now, family meeting. Me and Doug and a friend of his were gonna by into this co-op. We were gonna fix it up and sell it. The whole thing was gonna take a month tops. We would have doubled our money no questions asked. Except the guy took the money and split.
Bailey: How much money did you lose, Charlie?
Charlie: 12 [long pause] thousand.
Julia: Of your own money right?
Bailey: So much for your lectures on responsibility. Is this why you wanted control of all the accounts so you could blow it all yourself?

Charlie: Listen I got this idea. It says here there's a new band at the Armory and they're supposed to be really hot and I get off from the bar early. You free?
Kirsten: There must be something in the water. Suddenly everybody's interested in my social schedule. Actually I got 2 front row tickets to Liz Phair tonight.
Charlie: OK, that's just as good.
Kirsten: I'm going with George. He got them through his law firm.
Charlie: I can't believe you're going out with a lawyer. I mean isn't that kind of button down for you?
Kirsten: No, it's kind of perfect. The truth is I kind of owe it all to you. If you hadn't bailed out on me a couple of weeks ago, George and I might have never hooked up.
Charlie: If I could bring one ray of sunshine into your life...
Kirsten: You know, I thought we had something going Charlie, but you kind of weirded-out on me.
Charlie: I was trying to be a lot nobler then I actually am.
Kirsten: I'm not following you.
Charlie: Never mind it'll never happen again.

Charlie: So I take it Jill told you about our conversation?
Bailey: Yeah. Yeah, she did. And I can't believe you would just out of nowhere accuse her of being on speed!
Charlie: She's on speed, Bay.

Charlie: So what, it's one strike and I'm out with you?
Kirsten: I guess so, yeah! See, that's what happens when you cheat, and when you lie to me!

Charlie: So, how many?
Claudia: A couple....a few....some....six.
Charlie: Six? Six cavities? That's, like, 20% of your teeth, Claud!