Bailey: 65,000 dollars! Do you have any idea how much money that is?....It's 65,000 dollars!!!!
Julia: Can you say 'rich,' Owen?

Bailey: [about his crush on Kirsten] Any suggestions?
Will: Yeah. Snap out of it. Do you have any clue how to analyze the poem "To His Coy Mistress" in terms of its theme, metaphor, imagery and meter?
Bailey: Not off the top of my head.
Will: Well you better figure it out, cause if you spend the next 3 days mooning over this babysitter and blow this paper, you get put on academic probation and get benched from the team, and we lose another game. Ten other guys are gonna come to your house and do a job on your face so no girl will find you attractive again, OK?

Bailey: [Claudia's crying about Jill's death] Why are you crying?
Claudia: Because. Why aren't you?
Bailey: Would you please just get out of here, Claudia?

Bailey: [to Charlie, about feminine products]: Do you have any idea what wings are?

Bailey: [to Charlie] We'll give up whatever we have to to get by and we'll let everyone think you're this great guy just trying to hold his family together, who's like a father to us, even if we know it's a lie.

Bailey: [to Owen] Listen just to keep you up to date, and don't take this the wrong way, but I'm going crazy here. So unless I come up with some kind of nanny soon, I'm gonna have to sell you off to white slave traders. Now I know that's not how you pictured yourself growing up, but hey welcome to the club. Sleep well.

Bailey: All right, let's see here...these look good! Come on, let's get out of here.
Claudia: Bailey, these are tampons! Super plus! Jesus...there sure are lots to choose from.
Bailey: These have wings. Wings...what's up with that?

Bailey: Do you think it's always gonna be like this for us?
Julia: I don't know. Maybe.... maybe these are the good old days.
Bailey: [laughs] Yeah. Doesn't get much better than this, huh?

Bailey: Fine, who cares if I flunk math as long as you get to play in a sandbox with your stupid boyfriend!
Julia: Oh yeah, that's funny Bay, like you have the right to call anyone stupid!
Bailey: God, Jul, when did you turn into such a bitch?

Bailey: Girls switch boyfriends all the time.
Will: Well what are you going to do? Just call her up and tell her to break up with him? And go out with you instead?
Bailey: No, I'm gonna, you know... I'm just gonna... hang around her a lot.
Claudia: Yeah, you know... Just be there all the time.
Bailey: Yeah.
Will: Gee, why didn't I think of that.
Bailey: And then you know, eventually she'll fall for me.
Claudia: Like a ton of bricks.
Will: And why is that again?
Claudia: Duh... He's Bailey.

Bailey: Hey Charlie, you ever get the feeling the Gods just don't like us?
Charlie: All the time, Bay, all the time.

Bailey: I can't love anymore, it's too hard. So I'm not going to love anyone, and I don't want anyone to love me.
Charlie: That's too bad... you don't have a choice... because I love you, Bailey. I love you, man.
Season 2

Bailey: I don't know...it's like I'm trying to keep from drowning, and I keep getting reminded of how easy it's been for you.
Julia: It hasn't been that easy.
Bailey: But at least you have Justin.
Julia: Yeah...I guess.

Bailey: I'm sorry I missed your birthday. It's just that with Jill and everything, it was...
Claudia: More important. Yeah, I know.
Bailey: No. Not more important. But...I guess it seemed more urgent. I'm really sorry.

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.