I've had a few.
Wanna climb in the hot tob? Asked by some milf who was accompanied by a couple of teenage girls (all were attractive). The hotub was right off the highway and plugged in by an extension cord; that was probably the craziest part of the story; however, I was also surprised by the question.
"whatchya training for?!!!....WALKING?!!!!"
"How'd you let them girls get in front of you?!" Our girls team started their run quite a bit before us, and this guy asked this in a very backwoods boomhauer accent. Nobody understood at first, but I was, magically, able to translate for the rest of the team.
Also, this one old man on my home street used to yell "You can slow down, nobody's chasing you" every time he saw me run past him.