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
I just thought of another, it was asked by my mom to my sister, thankfully not me.
My mom asked my sister what a MILF was. My heart kinda skipped a beat and in my head was a "WTF!?!?" moment. The strange thing is that she came relatively straight out with the answer.
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.
I sudenly feel normal compared to you people... The strangest question for me is probably Are you german? Cause you look like you came from Paris... This was asked to me by...I can't remember now...
Once my friend ask me "Hmm, I wonder what you taste like. Can I bite you?" I even let him bite me (because I was curious myself). He said I tasted like soapy potatos.