Personally, from puberty through most of high school, I never approached any girls because I never had to--in my social setting it was totally normal and acceptable for girls to ask boys out, and I guess I was approachable enough, despite not being very popular, to get asked a fair amount. Yet I still had this culturally inherited concept that it should be me who was doing the asking, or at least learning how to do it. So I struggled with this a lot in my teenage years... part of the problem was that I also didn't have the stereotypical physical attraction to women, but a more personality-based one, so a lot of time was wasted trying to convert close platonic friendships into romantic relationships (maybe that works for some people, but not in my experience).
Ultimately, the woman I married was someone I approached without knowing her beforehand, but only after like weeks of making very mutual, not at all creepy eye contact walking back and forth on the same paths in the music center of our college campus. I think that's sort of the bare minimum: some signs of shared context, some shared interest or hobby, some smoke signals indicating mutual attraction. And for a minute I still thought maybe we were meant to be just friends, but obviously I was wrong, and part of how I know that is the way we met: with clear physical attraction established. This was all before dating apps, and I think I can see their appeal from that perspective; they reduce the uncertainty about "what kind of relationship is this going to become" to some extent.
Anyways, though, I'm pretty sure that I didn't have to put myself through the suffering of trying to "be a man" and build up the confidence to ask women out, because I was lucky to have a milieu in which they could comfortably take the lead. Heck, my wife might have been the one to break the tension eventually if it wasn't me. What I do regret, for sure, is the platonic friendships I lost with women during that phase in which I felt I was "supposed" to be converting them into girlfriends. The kind of reasoning that draws a direct line from changes in who is doing the asking out (for a variety of reasons) to male loneliness is really not helping any young men who are similarly confused.