Sheperd: I feel terrible, but I have to cancel our date tonight.
Sydney: Another woman?
Sheperd: No, I’ve gotta go to St. Louis and avert a massive airline strike.
Sydney: Boy, if I had a nickel for every time I heard that one.

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More from The American President

Lewis: I tell any girl I’m going out with to assume that all plans are soft until she receives confirmation 30 minutes beforehand.
Robin: And they find this romantic?
Lewis: Well, I say it with a great deal of charm.

Sydney: Two hundred pairs of eyes are focused on you right now, with two questions: “Who’s this girl, and why is the President dancing with her?”
Sheperd: First of all, the 200 pairs of eyes aren’t focused on me. They’re focused on you. And the answers are “Sydney Ellen Wade” and “Because she said ‘yes.'”

Sheperd: I gotta get her flowers.
Lewis: Here?
Robin: Now?
Sheperd: I broke our date. This is what men do.
Robin: It’s not what men do. I know no men who do that.

Sheperd: I want to send some flowers, Janie. I want to do it myself. I don’t want to staff it out, and I don’t want to issue an Executive Order. I just want a phone number.

Sydney: What do Lewis and Robin think?
Sheperd: Brutus and Cassius? They want me to get into the character debate and mix it up.
Sydney: Lewis and Robin are very smart.
Sheperd: Sydney says you guys are really stupid.
Sydney: I didn’t say that!
Sheperd: She’s questioning your loyalty.
Lewis: Hell, I question it all the time.