Sheperd: Are you nervous?
Sydney: No.
Sheperd: Good. My nervousness exists on several levels. Number 1 — and this is in no particular order — I haven’t done this in a pretty long time. Number 2: Any expectations you might have, due to the fact that I’m, you know…
Sydney: The most powerful man in the world?
Sheperd: Exactly, thank you. Just so you remember that’s a political distinction that comes with the office. I mean, if Eisenhower were here instead of me he’d be dead by now.

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More from The American President

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.

Sheperd: Janie, make a note. We need to schedule more events where somebody gives me a really big fish.
Janie: Yes, sir.
Sheperd: Janie, I was kidding.
Janie: Of course, sir.