Charlie: So, uh, Betsy, maybe we can get the boys together for a little play date sometime.
Jake: I don't want a play date with some stupid kid just so you can have sex with her!

Charlie: So, what are you doing for dinner?
Lisa: You're shameless.
Charlie: Thank you.
Lisa: It's not a compliment.
Charlie: Whatever. What are you doing for dinner?
Lisa: Charlie, a lot has changed.
Charlie: I know. I'm older and wiser, and you're hot and on the rebound!

Charlie: This is a Rolex! You sold me out for a watch!
Alan: Hey, I did not sell you out for a watch. I sold you out for a genuine Swiss chronometer. Stainless steel submariner, waterproof up to 300 meters, and look, it winds itself. [repeatedly shakes his left hand]
Charlie: Put it on your right arm, it'll run forever.
Alan: Oh hey, good idea!

Charlie: This relationship isn't based on sex!
Berta: Not based on sex? Well, unless she sweats Bourbon and farts $100 bills, what exactly is going to keep you together?

Charlie: Until he [Jake] was ten, I had him convinced that swizzle sticks were money!
Alan: Hey, hey, uh, uh, speaking of swizzle sticks, ha-- have you considered eloping to Vegas?
Herb: Hmmm. No, we haven't--
Alan: No, I know what you're thinking, "tacky-tacky," but... uh, it's classy and very romantic.
Charlie: Yeah, some of the hotel rooms have those big mirrored walls. It's like watching your ass bob up and down in IMAX.

Charlie: We had fun last night, though, right?
Lydia [sarcastically]: Oh, terrific. What woman doesn't enjoy pleasing a man who falls asleep while he's in the middle of reciprocating?
Charlie: Well, that explains why I dreamt I was kissing Abe Lincoln.

Charlie: We'll be lucky to leave here [Evelyn's house] with all of our limbs and gonads!
Jake: What's a gonad?
Charlie: You are.
Jake: So it's bad.
Alan: You're not a gonad.
Charlie: Says the other gonad.

Charlie: We've got a real problem here.
Berta: What do you mean "we"? [walks away]

Charlie: Well, I want it on the record that if the kid was running a blackjack game under the bleachers, he didn't necessarily get the idea from me.

Charlie: Well, that's the difference between 'wife' and 'ex-wife'. With 'ex-wife', you don't even have to pretend to care.
Alan: I'm sorry, but I can't be that callous.
Charlie: Have you even tried?

Charlie: Well, what if you were dating?
Alan: But I'm not.
Charlie: But what if it looked like you were dating?
Alan: Oh, oh, you mean-- no, no way. I-- I'm not gonna let you fix me up with one of your bimbo girlfriends.
Charlie: OK, forget it.
Alan: She'd have to be really pretty, like a... like a ten. And young, like a twenty.
Charlie: Anything else?
Alan: Uh, and smart. Uh, and a sense of humor's important. Uh, well-read, uh, good with kids, uh, non-smoking, of course... ooh, and, uh, easy on the piercings. Nothing south of the equator.
Charlie: You're mighty picky for a guy with an adult newsstand in his sock drawer.

Charlie: What are you looking at me for? Just stay out of her neighborhood!

Charlie: What I'm saying is, you got nothing to complain about. You got your food in my refrigerator, your car in my garage, and your stupid flowered towels in my guest bathroom!
Alan: Hey, those towels are very pretty! They brighten up the whole room!
Charlie: They're gay, and they scream "civil union"!
Alan: They do not!
Charlie: "We're here, we're queer, dry your hands on us!"

Charlie: What I've wanted to ask you is, "Do you think I've been a good role model?"
Jake: Are you kidding? You drink, you gamble, you have different women here practically every night. You're the best role model a guy could want!
Charlie: You think so?
Jake: Yeah, they should put your face on money.
[about condoms]

Charlie: What is that old witch doing here?
Alan: Old witch? She's a charming woman!
Charlie: Of course she's charming. They're all charming. That's how they lure you into their houses made out of candy and gingerbread.