“- Robb: See, Mike, the only difference between giving up and not giving up is if you take her back when she wants to come back. But you can't do anything to make her want to come back. In fact, you can only do stuff to make her not want to come back.
- Mike: So the only difference is if I forget about her or just pretend to forget about her?”
Ron Livingston - Rob
Jon Favreau - Mike

“- 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