- Mary: We broke up decades ago. Long before you were born. He just can't remember.
- Ray: But you can. Right? You knew? That's something you might want to bring up on the first date, Mary. "I don't like to travel. I'm allergic to cats. I'm immortal". Okay? Those are some of the things you might want to give a little heads-up on.

Charlize Theron - Mary
Jason Bateman - Ray

You know what's the worst thing about somebody breaking up with you? It's when you remember how little you thought about the people you broke up with and you realize that is how little they're thinking of you. You know, you'd like to think you're both in all this pain but they're just like "Hey, I'm glad you're gone".
Ethan Hawke - Jesse

“Everything is gone from me but the certainty of your goodness. I can't go on spoiling your life any longer. I don't think two people could have been happier than we have been.”

Nicole Kidman - Virginia Woolf

“- Sue: You're gonna have to start deviating. He's breaking up with you.
- Paula: What?
- Sue: The only reason he ever brings girls home to meet us is 'cause he's gettin' ready to dump 'em.”
Kathy Bates - Sue
Sarah Jessica Parker - Paula

“- Jerry Falk: Where's the rifle? I need the rifle. I'm going to blow my brains out!
- Amanda: Oh, don't be so middle class!”

Jason Biggs - Jerry Falk
Christina Ricci - Amanda