- 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

“- 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

“- Telly: The best way to get over an old man...
- Ormandy: ...is to get under a new one!”
Royale Watkins - Telly
Kym Whitley - Ormandy

“- Max Fischer: I thought you dumped me for Blume, then I thought...
- Rosemary Cross: I never dumped you, because we were never going out.”
Jason Schwartzman - Max Fischer
Olivia Williams - Rosemary Cross