Alan: Judith's changed, Charlie. She's...she's a different woman.
Charlie: Different than the one who threw you out of your house with your nuts in a to-go bag?
Alan: That's a little graphic, don't you think?
Charlie: I'm an artist, Alan. I paint with words.
Alan: You're a lush, Charlie. You paint with vomit!

Alan: Just 'cause you're reading a dance magazine doesn't make you a dancer.
Berta: Why not? You're a monster boob.
Alan: Will you both stay out of my room?!

Alan: Knock 'em dead at the audition.
Kandi: Thanks. And thanks for lending me your chiropractor coat. It makes me feel like a real doctor.
Charlie: Now you know why Alan wears it.

Alan: Look, don't worry, you'll grow into it.
Jake: Why couldn't I get clothes that fit now?
Alan: Yeah, well, quit going through puberty and we'll talk about it.
Jake: Quit been so cheap and we'll talk about it! [leaves]
Alan: Hey, hey, watch your mouth!
Charlie: Hard to punish him for telling the truth.

Alan: Looks like you had a tough night.
Charlie: No, the night was great. It's the morning that's killing me!

Alan: My point is that you're gonna leave her [Melissa] with bad memories that can be erased by removing herself from anything that reminds her of you, like me.
Charlie: Is that what you're worried about, Bunky?
Alan: Yes, that's what I'm worried about! What do you think I was worried about? What else would I be worried about?
Charlie: Well, let's see: your receding hairline, your semi-literate son, your budding man-boobs... but that's just off the top of my head.

Alan: Nevertheless, I am Jake's father, and I believe that childhood should be a time of innocence.
Charlie: I agree, childhood should be a time of innocence. And Bambi's mother shouldn't die, and lap dances should be complementary after the fifth cocktail, but that's not the world we live in. This party tonight is the initial round in a lifelong process of sexual elimination.
Alan: Oh, really?
Charlie: Think of it as musical chairs, but when the music stops, the guys who have a clue are sitting on a woman instead of a chair. The guys who have no clue? They'll spend their teenage years-- well, I certainly don't need to tell Dungeon Master Alan.

Alan: Now, I have been to a lot of these things with Mom, and I know you think it's gonna be bad, but believe me, it's gonna be worse than you can even imagine.
Charlie: You're really enjoying this, aren't you? You just love seeing me unhappy.
Alan: Yeah. I mean, did you feel sorry for me when I had to wear that cowboy outfit to her celebrity AIDS hoedown?
Charlie: That was different.
Alan: How?
Charlie: It was you.
Alan: Yeah, well, now it's you. Yippie-ki-yay, mother-accompanier.

Alan: Now, what year did Magellan circumnavigate the globe?
Jake: It's not gonna be on the test.
Alan: Maybe not, but it wouldn't hurt for you to know it anyway.
Jake: Why would I want to know something I don't have to?
Alan: Because maybe you'll need to know it in the future.
Jake: Well, then that's when I'll learn it!
Alan: Why can't you just learn it now?
Jake: 'Cause there's only so much space in my brain that if you put Magellan in there, I might forget my locker combination.

Alan: Oh, are you, uh, starting that book report already?
Jake: Just making notes.
Alan: Good for you! What do you have so far?
Jake: Lord of the Flies is kind of like Survivor, but with kids.
Alan: Huh! That's, uh... that's an interesting analogy! Uh, what's your favorite part?
Jake: Um... when the first kid gets voted off the island?

Alan: Oh, Charlie, don't you think you need to slow down a bit?
Charlie: Why would I want to do that?
Alan: Well, come on! Is-- is this lifestyle actually making you happy?
Charlie: Let me answer that question with another question: Who would you rather be, you or me?
Alan: You're kidding, right? You have two black eyes and you're perched on a scrotum cozy. [reluctantly]: You.

Alan: Oh, Charlie. Your penis is no match for my technology.
[Charlie enters Alan's room]
Charlie: OK, I know what you're doing, now quit it!
Alan: What I'm doing? Whatever do you mean?
Charlie: You're text-blocking me.
Alan: Hey, I can't help it if Chelsea finds me witty and urbane.
Charlie: Keep it up, and she's gonna find you bloody and homeless.

Alan: Oh, come on, Charlie, so you struck out with a woman. It happens. Believe me, it happens! And when it does, the best thing to do is to pick yourself up, dust yourself off, and curse God for making you the way you are.
Charlie: All right, forget it, I don't need you. I'll call her [Linda] myself. [leaves]
Alan [to God]: Sorry about the "curse God" stuff. But we both know I'm not your best work.

Alan: Oh, let's face it: we're both too old for the MTV lifestyle.
Charlie: MTV? Did they just defrost you?

Alan: Oh, this looks interesting: "Two-bedroom, needs work, up-and-coming neighborhood." Wh-- what does that mean, uh, "up-and-coming neighborhood"?
Evelyn: It means the realtor couldn't move the house saying "drug-ravaged battlefield".