Hasn't happened yet.
All throughout my teens I was unpopular, was really shy, and had low self esteem, so I basically didn't even try. When I started college, I was still really shy and didn't do anything social, but I did ask out a few girls, but they either said no or shit happened. And that's the story for the majority of women I've asked out. There was one woman a mutual friend set me up with, but I wasn't physically attracted to her, and I wasn't ready to be with someone I wasn't physically attracted to.