Great stories!
Here's my contribution...
Last year I'd just gotten this old (probably older than I am) bike from goodwill as a "project" bike and was taking it out for a ride on a bike trail after rendering it usable. Half way up a fairly steep hill I meet this guy, probalby about 70, coming down the hill, sweating and huffing like anything. I continue on my way, not thinking much of it, but I'm sure feeling my own ego inflating a bit ("stop that! that's not nice, he's an old guy!"), when near the top of the hill he overtakes me. (I'm pretty sure he reached the bottom before turning around). He proceeds to stay far enough ahead of me that I thought he'd completely dropped me, but on the rare straight stretches I could see him in the distance.
I eventually cought up, only to hit a rediculously steep section of the trail and have him blow by me, never to be seen again.
and the worst part? He was jogging!