Charlie: All right, then... how about a quickie for old times' sake?
Mia [giggles]: Please. Charlie, I think you're a terrific guy. You're smart, and handsome, and talented...
Charlie: All good arguments for the quickie.

Charlie: And did she [Evelyn] or did she not say that I'm a lazy-ass schlock jingle writer who wasted thirteen years of piano lessons that she paid for by marrying a series of men with large wallets and small penises?
Mia: Yes, that was mentioned. But it's only natural for someone who loves you to want to see you live up to your potential. I mean, do you really want to be known as the guy who writes songs about adult diapers?
Charlie: Hey, it's better than being known as the guy who wears them.

Charlie: Are you aware that I'm a misogynist?
Evelyn: Really? I raised you Episcopalian.
Charlie: This isn't funny! My anger and mistrust towards women starts with you, which wasn't a problem until it spilled over into my sex life.
Evelyn: So, you're blaming Mummy because Little Charlie can't come out and play?
Charlie: OK, first of all, we don't call it "Little Charlie"!
Evelyn: What do we call it, darling?
Charlie: We don't call it anything!
Evelyn: Well, when you were a baby, we called it "Mr. Pinky".
Charlie: I may never have sex again.
Evelyn: Oh, wait a sec, Mr. Pinky was the cat. What did we call your penis?

Charlie: Did she [Rose] just use the front door?
Alan [staring in disbelief]: Uh-huh.
Charlie: She never used the front door before.
Alan [still staring in disbelief]: Uh-uh. What happened out there?
Charlie: Well, I, I, I told her I was going to marry Mia and I think I could actually see her medication stop working.
Alan: What do you think she's gonna do?
Charlie: The question isn't what, it's when, and how I'm gonna enjoy my honeymoon with my testicles glued to my ass crack.

Charlie: Face it Alan. What can you bring to the table other than a lifetime of failure with women?
Alan: It's not a lifetime yet!
Charlie: I, on the other hand have a wealth of experience.
Alan: He's [Jake's] twelve! He doesn't need to know how to choreograph a three-way!

Charlie: Forget it, Alan. I only do the après sex chat with people I've just had sex with.
Alan: Come on, she's [Kandi] playing Family Feud with her toes!
Charlie: I don't care if she's playing banjo with her nipples!
Alan: But I-- I need to communicate after lovemaking. I-- I need to share.
Charlie: Well, maybe you should have thought of that before you started boinkin' a girl with the IQ of Tickle Me Elmo!
Alan: Fine. [walks away from Charlie toward Berta] Hey, Berta, how's it going?
Berta: Back off, Zippy. If you want pillow talk, you gotta spoon me first.

Charlie: Hey, Alan. [to Jake]: Matey.
Jake: I'm not a pirate.
Charlie: You're not a gangsta, either. You're a dorky white kid with a Cub Scout bandana on his head. [takes it off]
Jake: Yo, hate the game, don't hate the playa.

Charlie: Hey, here's a fun fact. You're sleeping with a girl who was born when you were in junior high, and yet there's a good chance she lost her virginity before you did.
[Alan scoffs, shakes his head, and then starts to do the math in his head]
Charlie: And here's another fun fact. I'll bet she's had sex with more girls than you too.
Alan: [scoffs again, and again does the math and smiles] That is a fun fact!

Charlie: Hey, If you got her [Norma] pregnant, we can get a full page in Ripley's.
Alan: Give it a rest, Charlie.
Charlie: Oh, come on, I've been working on these all morning! Listen to this: "Her first car was a chariot." "She called her first husband Hun, 'cause he was one!" "Her first Christmas was the first Christmas." "Likes to take long walks on the beach after crawling out of the ocean and growing legs." "Her birthstone was lava." And finally, "The Big Bang"! I don't have a joke for that but I know there's something there!

Charlie: Hey, listen, about this "living without sex" thing, I was hoping you can give me a little advice.
Alan: Me? What would make you think of me?
Charlie: Well, I figured you get laid less often than a boil-covered dwarf, am I right?
Alan: I don't have the actual statistics, but go on.
Charlie: Well, you must get really frustrated. I mean, how do you stop yourself from, you know, running a red light and then taunting the cop 'til he shoots you?
Alan: Ah, good question. Uh, I found that the best thing to do is to focus on your career, uh, get a hobby, uh, become involved in community activities, and at the end of the day, if you have any energy left, find a quiet space and yank it like a monkey in a mango tree.

Charlie: I don't have a lot of faith in psychiatry as a science. I think some of the drugs you're pushing are interesting, and I'm all for messing around with brain chemistry. I mean, that's how I got through high school. But in my experience, popping pills doesn't relieve social anxiety quite as well as, say, bourbon and Marvin Gaye.
Dr. Freeman: Now I get it. You're desperate, and I'm full of hooey. So in the words of Marvin Gaye, "What's goin' on?"
Charlie: Everything I say is confidential, right?
Dr. Freeman: Whatever you say stays in this room.
Charlie: Kind of like Vegas.
Dr. Freeman: Well, except there's no way you're leaving here with more money than when you came in.
Charlie: Yeah, like Vegas.

Charlie: I think I might be in love with Mia.
Alan: Big deal. You've always been in love with you-a.

Charlie: I'm buying the little wiseass a $75 haircut, and he's taking shots at me?!
Alan: You said it yourself: He has to find his own look.
Charlie: Yeah, well, let him find it on somebody else's MasterCard!
Alan: Come on, look at his point of view.
Charlie: What's his point of view?
Alan: Well, put overalls on you, and you do look kind of like the Big Boy. Stand like this for me: [poses like a Big Boy statue]

Charlie: I'm gonna tell you something that'll serve you well for your entire life.
Jake: Like when you're peeing outside, always face downwind?
Charlie: Better. By the way, what the hell were you thinking?
Jake: I was thinking, "Boy, I hope that's really warm rain."

Charlie: I've just been seeing this ballet dancer, and I think she might be the one.
Evelyn [to Alan]: Drunk?
Alan: He says no.
Berta: I think it might be one of those designer drugs. Charlie? [slowly]: What did you take?
Charlie: I'm serious. We've been seeing each other for over a month, and we're waiting to sleep together until our relationship has a solid foundation.
Evelyn: Well, we can rule out ecstasy. That's a powerful aphrodisiac. I've heard.
Jake: Nowadays, we're supposed to say "African-American-disiac".