I definitely have a couple of pretty rough moments. The first one that comes to mind ... I was a young midshipman at the US Naval Academy. USNA policy was to use midshipmen to enforce basic security at various events -- basketball games, football games, and the like -- to ensure against people wandering in one of the many alternate entries without a ticket. I was stationed at a roped off entryway that really looked like it should have been an authorized entry, but wasn't. People would wander up and try to get around me, and I'd say, "I'm sorry, sir, you can't go this way." Then I'd politely direct them to one of the authorized entry points.
So I see a guy come in the outer doors. He's a little older, and kind of balding, and looks vaguely familiar, but I can't place him. He walks straight towards me, not even slowing down. I snapped briskly from "parade rest" to "attention," raising the hand in the universal symbol of "stop," and gave him my standard line: "I'm sorry, sir, you can't go this way." He looked vaguely amused at this childish midshipman as he responded, "But I'm The Admiral." And then I recognized him -- the 4-star Admiral in charge of the entire Academy. Ooh.
Ok, the other one that's in pretty close competition: Valentines Day. First "real" date with a girl. She knows I have a Porsche 911, but the parts I needed to get it back running hadn't arrived yet, so I had to pick her up in the beater Honda -- strike one. She had a real steep driveway, and I managed to kill it trying to pull out -- strike two. Then, my car had a weird intermittent warm-start problem (turned out to be the FI relay), and the car wouldn't start -- strike three. I own a Porsche 911, but can't pick you up in it because it's broken. And I can't drive stick. And I can't even maintain my daily driver well enough that it will restart on command.
Oh -- same evening: it's raining, and I'm a gentleman, so when we finish dinner and head back outside, I tell her to wait at the entry of the restaurant while I go get the car. I dash out into the parking lot, unlock the driver's side door, get in, and drive up to the covered entryway area. Before she can open her own door, I jump out and dash around the car to get the door for her ........... but I forgot to unlock it. (sigh) and there were people watching, too. At least I drew a laugh on that one.
So that's three, but they're worth it.