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Alan: Don't you dare feel sorry for me. This is what an adult relationship looks like, Charlie. People get comfortable with each other and they develop a routine, and if it's not always fireworks and explosions, well that's a reasonable trade for a warm, collegiate partnership.
Charlie: You poor, poor bastard.

Jake: She is kind of cute.
Charlie: Why don't you go talk to her?
Jake: I don't know what to say.
Charlie: That's never stopped you from runnin' your mouth before.

Charlie: You're supposed to meet her there.
Alan: Why?
Charlie: What do you mean, "Why?" You're gonna break up with her and then drive her home? You'll need the Jaws of Life to get her out of your car.
Alan: You didn't say anything about that.
Charlie: It's common sense. Do you know why Custer and Sitting Bull didn't share a pony to Little Big Horn? Because they knew there were gonna be hurt feelings, and the ride home would be awkward!

Alan: I'm in trouble here, Charlie. How do I get out of a stagnant, joyless relationship?
Charlie: If I knew how to do that, you wouldn't still be living here.

Charlie: Tell you what, I'll be your wingman. I'll go over and engage the mom in conversation. Then, after I've greased the wheels, I'll give you a signal. You saunter over and work your magic.
Jake: "Saunter?"
Charlie: Walk.
Jake: Well, then, just say "walk." You don't have to make up words.

Jake: In ultimate fighting they kick, they elbow, they get a guy down and smash his head in the floor. These guys just dance around and barely hit each other.
Charlie: Okay, okay, listen to me. Boxing is a science. Boxers don't just wail on each other: they strategize, feel each other out, wait for an opening.
Jake: Gay.

I once handed a date my Visa so she could pump gas for me, and on my next statement, there were charges for a boob job and a PlayStation 3. And I never got to play with either one of them.


Alan: I loved Charity Kirschenbaum and you stole her right out from under me!
Berta: He's speaking metaphorically, right?
Charlie: Yeah... he was never on top of that.

I really shouldn't be giving [Jake] advice that will help him reproduce.

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