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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Sydney: I want to say something, but I’m gonna fumble it a little bit, so I’d just like you to wait till I’m done before you respond. I’m in love with you. I’m certain of it. And I want to be with you more than anything. But maybe things would be better for you if I disappeared for a while.
Sheperd: Things will be better when I pass a crime bill. And Sydney, if you disappeared, I’d find you.

Lewis: Can I just say, to return to the subject for one moment, that it might be easier to fight a war on drugs if we weren’t arming drug dealers?
Sheperd: Lewis, we’ve gotta fight the fights we can win.

Sydney: Your dad says you’re studying the Constitutional Convention.
Sheperd: She’s not having any fun, though.
Lucy: Dad–
Sydney: You’re not having fun?
Lucy: This is a nightmare. This is a social studies nightmare.

Gill: Mr. President, militant women are out to destroy college football in this country.
Sheperd: Is that a fact?

Sheperd: No, keep going. I liked what you were playing. What’s it called?
Lucy: Scales.
Sheperd: Well… you play it with gusto!