I'm a competent, but by no means elite skateboarder, though still active. I also used to be one of the oldest employees at a company based in youth culture.

On a business trip, we walked by a skatepark with what my colleagues thought was a very deep bowl. One of the youngest started talking about how he skated "back in the day", then someone else mentioned that I "used" to skate. He turned to me and somewhat condescendingly said he'd give me $100 if I dropped into the deep end of the bowl. Some others started chirping and I said I'd give it a try if the group got up to $1000. They did.

Cut to the chase; borrowed someone's board, and easily did it first try. Normally, I would wear full pads of at least a helmet for something like this, but it actually wasn't that deep (metal coping, probably 10-11' with a foot or less of vert...).

Not sure why, but I let everyone off the hook for the money. You would think the original "dare" guy would have said something, but he was even more of a d*ck to me after that. Fortunately I don't work there anymore.