Good on you ! I was never able to overcome this. I was lucky to meet my wife who is just as awkward, otherwise it’s safe to say I wouldn’t have had the courage to ask anybody out until much later in life. I remember a high school classmate telling me more or less verbatim what you said above : “ask, if she says no, so what?” unfortunately that never helped. Some of us were simply too shy, too far removed from social norms, or perhaps too autistic to act on that. Human interactions are a mystery to some of us. In fact, what he said made things worse for me, because it made me realize just how developmentally late I was, and seeing how easy it was for some people to get over the initial apprehension furthered my feelings of isolation.