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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Lewis: Who are we calling, sir?
Sheperd: I’m calling the Organization of the United Brotherhood of It’s-None-of-Your-Damn-Business, Lewis. I’ll be with you in a minute.

Sydney: How can you keep quiet? How do you have patience for people who claim they love America but clearly can’t stand Americans?

Sheperd: Lewis, however much coffee you drink in the morning, I want you to reduce it by half.
Lewis: I don’t drink coffee.
Sheperd: Then hit yourself over the head with a baseball bat, would you please?

Sydney: Leo Solomon has serious concerns about my exploring a social, you know, scenario, with the President of the United States.
Sheperd: Yeah, well, when you put it that way, it doesn’t sound that great to me either.

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.