Mine would be walking by hobo and him asking me what "Spaceship would you own, the 123, 989, or 545" the reason I have memory of that is I just remember strange things
The weirdest question I got was Is it ok to have a lover? A girl from my school asked me that after someguy,who had a baby with another girl,told her that he had feelings for her.I think my answer was Errr...No.
HOLY HELL, asking someone that in public is wrong, and 99.9% of guys would lie anyways...
I once had three girls come up to me in high school and ask me that. They then asked if I wanted a threesome, which by my count if they meant me and the three of them didn't quite add up right.
There was a vagrant we so lovingly named Dude, that lived behind our local convenient store who asked me while I was standing inline alone buying some beer. He turned to me and said "gentlemen, have you ever been on the back a motor cycle going 67... hundred miles per hour?" I have been asked many weird questions but this one was the first that popped in my head.