When Pres. Shepherd is looking to win back Sydney.
President Shepherd: I want a plain, ordinary, non-bullet-proof vehicle!
A.J.: And how do you plan to [get Sydney back], sir?
President Shepherd: Well, I haven't worked that out yet. But I suspect groveling will be involved.
Shepherd develops a liking for Sydney when she has several foot-in-mouth moments during the first day they meet, including a The Exit Is That Way in the Oval Office, not to mention starting off with a priceless Right Behind Me moment as he comes in while she's in the midst of delivering a tirade about him:
Sydney: Your boss is the chief executive of fantasy land!
Shepherd: Well, let's take him out back and beat the shit out of him!
Shepherd attempts to order flowers for Sydney himself to the confusion of his staff. A big giant ball of Hilarity Ensues. To elaborate:
First, his personal aide becomes rather worried that it is a reflection on her work performance that the president wants to send the flowers himself, rather than make her do it. Lewis tries to nose in on who the president is calling, for which Shepherd shoos him out of the office. And when he finally manages to make the call the the florist, the sales person hangs up when he says that he is the President of the United States. He finally does get her flowers — from the White House Rose Garden.
Which becomes a Brick Joke: sometime later, Shepherd makes a personal visit to the florist and mentions that the President of the United States did make the call. The florist faints on the spot. "Yep, she remembered."
Sydney tries to bail out of the White House early in the morning after spending the night, but the press and staff are already in full tilt. The staff tries to figure out an exit strategy for Sydney while quickly greeting her as they barge into the President's bedroom one by one. You guessed it, Hilarity Ensues.
The state dinner discussion of Julius Caesar, leading to Shepherd slapping the table and declaring, "More beheadings at the White House!"
Lewis is hounding President Shepherd about the speech he gave the night before, and Shepherd tries to hold him off:
President Shepherd: Lewis, however much coffee you drink in the morning, I want you to reduce it by half.
Lewis: I don't drink coffee, sir.
President Shepherd: Then hit yourself over the head with a baseball bat, would you please?
The Sydney Issue:
Robin McCall: How do you want me to handle the Sydney issue?
President Andrew Shepherd: "The Sydney issue"?
Lewis Rothschild: We should have a consensus on how the White House is going to handle it.
President Andrew Shepherd: Well I sure hope the Sydney issue refers in some way to a problem we're having with Australia, because if it's anything else-
When Sydney meets with Shepherd to break off their relationship (before she ends up doing the opposite), she gets flustered with Andrew's light-hearted snarkery and starts to raise her voice irritably, which Andrew still takes in jovial stride:
Shepherd: Are you raising your voice to the President?
And then this exchange after their night together, before Sydney departs for home amidst a press frenzy:
Andrew: I'm sorry, we'll do this better next time.
Sydney: I'm no expert, but I thought we did it pretty good this time.
Shepherd: Good. My nervousness exists on... several levels. Number one, and this is in no particular order, I haven't done this in a pretty long time. Number two, uh, any expectations that you might have, given the fact that I'm... you know...
Sydney: [approaching seductively] The most powerful man in the world?
Shepherd: Exactly, thank you. I think it's important you remember that's a political distinction that comes with the office. I mean, if, uh, Eisenhower were here instead of me, he'd be dead by now... and number three...
Shepherd trying to get a feel for what Sydney thinks of him:
Shepherd: She didn't say anything about me?
A.J.: No, but I could always pass her a note before study hall.