Sometimes at work while I'm checking out people's items I whisper to myself. "Oh god, what have I done."
You should see the people's faces as they frantically look at the monitor to see where I -blam!-ed up. Then I scan the items quicker so they can't read fast enough. Then they get all freaked out and spend an hour reading their receipt before they realize that nothing happened.
So what do you guys go to screw with people?
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One of my best friends and I put on suits, drove to a city we've never been to before, and decided that we would pretend to be random professions for the day. The best was building inspector. We went into some tall government building with the goal of taking the elevator to the top floor - because that's what you do in tall buildings. Our inspector story got us through security without IDs so we took out a clip board and started "taking notes." When we finally got to the elevator we got off on a random floor for no other reason than to be random, inspected, and then went back and made our way to the top. The elevator opened into a narrow hallway that was blocked by two armed guards. So we didn't seem suspicious, we stepped out and started discussing and making notes about the light fixtures right in front of them. After a minute we slipped back into the elevator and cracked up all of the way down. Then we went to a department store and convinced the manager that we were investors, owned our own chain, and were probably going to buy them out. That day was a blast.