Romeo Posar: Now THAT was a defining moment. And the definition was "shit."
Roy 'Tin Cup' McAvoy: Sex and golf are the two things you can enjoy even if you're not good at them.
Doreen: You're not one of those women who tries to fix men, I hope. I mean, men cannot be fixed, and especially him.
Roy 'Tin Cup' McAvoy: You know why I still hit that shot?
Romeo Posar: Yeah, because it's the only way you could beat Dave Simms.
Roy 'Tin Cup' McAvoy: No.
Romeo Posar: 'Cause it was that look in your face...
Roy 'Tin Cup' McAvoy: I hit it again because that shot was a defining moment, and when a defining moment comes along, you define the moment... Or the moment defines you.
Molly: Is this normal for him?
Earl: Well, the words "normal" and "him" don't often collide in the same sentence.
Dr. Molly Griswold: I'm a, like, terrible shrink, probably. I should have never gotten out of real estate, shit, actually, I should have never left Ohio for that cowboy in Amarillo, but... Have you ever been to Amarillo?
Roy 'Tin Cup' McAvoy: Cowboy?
Dr. Molly Griswold: Yeah. It's not as romantic when you're actually with one, trust me.
Romeo Posar: Look, boss, I only got one rule. And that's never bet money that you don't have on a dog race with an ex-girlfriend who happens to be a stripper.
Roy 'Tin Cup' McAvoy: I assume I have the confidentiality of the doctor-client privilege in regards to this outfit?
Earl: You the man, Roy. You are definitely the man.
Clint: The man needs a ride home.
Molly: Why do men always insist on measuring their dicks?