“- Roy O'Bannon: I feel like there's this gap between us. It's like I'm a cowboy, you're an Indian. You say wampum, I say money. It is so important, I just think that...
- Indian Wife: [kisses Roy] Shut up, Roy. You talk too much.”
Owen Wilson - Roy O'Bannon
Brandon Merrill - Indian Wife

“- Courtney Blumenthal: What are you doing?
- Montgomery 'Monty' Kessler: I'm ending our friendship.”

Moira Kelly - Courtney Blumenthal
Brendan Fraser - Montgomery 'Monty' Kessler

“Yeah, it's all so hot three days in!”

Cynthia Nixon - Miranda Hobbes

“- Lenny Feder: Roxanne, I have made out with about 25 girls in this very spot and I want you to be number 26.
- Roxanne Chase-Feder: As long as I am the last.”

Adam Sandler - Lenny Feder
Salma Hayek - Roxanne Chase-Feder

“I have wasted thousands and thousands of kisses on you, kisses that I thought were special because of your lips and your smile and all your color and life. I used to think that was the real you, when you smiled. But now I know you don't mean any of it.”
Liv Tyler - Faye Dolan