“- Paula: I'm Paula.
- Tripp: I'm Tripp.
- Paula: You know, usually I don't sleep with someone on the first date.
- Tripp: I don't think this counts as a first date.”
Sarah Jessica Parker - Paula
Matthew McConaughey - Tripp

“If you're out with this girl and even thinking about getting laid, you're finished, cuz women can smell an agenda like shit on a shoe.”

Donal Logue - Dex

“- Sandy: Oh, my... that kind of evening?
- Lauren: Well, not the kind you're used to; no money changed hands!”

Bette Midler - Sandy
Shelley Lee Long - Lauren

“- Dean Proffitt: You jumped my bones the first night we met!
- Annie: We did it on the first date?
- Dean Proffitt: Couldn't call it a date really, we just did it in the parking lot of the 7-Eleven
- Annie: I'm a slut.
- Dean Proffitt: What did you say?
- Annie: Nothing.”

Kurt Russell - Dean Proffitt
Goldie Hawn - Annie

- Anita: Guess who I did it with last night?
- Josie Geller: Roger from Op/Ed?
- Anita: Aww... Who told you?
- Josie Geller: You did. You said, and I quote "Tonight I have a date with Roger from Op/Ed, and I'm gonna do it with him".
.

Molly Shannon - Anita
Drew Barrymore - Josie Geller