Yes, really.
Her hair then was mostly grey with some light brown - she started going grey in high school, and couldn't be bothered with it. It looked amazing... these days it's completely white, and looks even more amazing. She gets women asking her where she gets her hair done and they get mad when she "won't" tell them. She just says "I don't do anything to it, just wash it and brush it."
I guess the lesson here is that you should NOT pre-judge a woman based on her looks. My wife is rare, but they're out there. Bonus for me: She doesn't wear makeup, and doesn't like jewelry. I win!
So you'd rather not take a chance and ask out a beautiful woman based on your so-called "fair assumptions"?
Who's the only one that loses here? What have you GOT to lose? Just go for it.