I think there is something of a disconnect for some men with changes in what is culturally acceptable when it comes to mating as well as holdovers from traditional structures.
There are definitely women out there who will ask guys out, but I'd wager, based on my own circumstantial and spotty experiential evidence in my culture, that it's men's responsibility to initiate has generally remained the case. I think guys who are less adept socially/are timid have difficulties resolving this facet of dating with the decreasing tolerance for overstepping boundaries--some dudes get wet feet because they realize they have to initiate but scare themselves out of it because, compounded with their inherent difficulties in socializing, they now build up this ridiculous fear-based narrative wherein their social clumsiness leads to misinterpretations which wind up screwing them way harder than a simple rejection.
This fear, of course, is unfounded. But I do think the mating initiator in most cultures, whether it be men or women, often relies on 'primal' methods in order to go after potential mates--aggressiveness, shows of power, confidence...When it comes to mating we really haven't moved far away from the schemes of any of our other animal brethren--yes we have money, cars, nice clothes, ambitions instead of colorful plummage, but things are otherwise the same--the old playbook. When you utilize this with restraint, all is well. When you let power go to your head and convince you that things are more animal than they really are and that this sort of behavior is always permissable you wind up like one of our lovely VCs here. That is still the case, and dating is of course nuanced--you have to utilize these peacock techniques but recognize a rebuff when you see one and cease your little dance. I think some guys fail to see the nuance and then read these stories correctly condemning jackasses for their behavior but lack the social understanding to realize this doesn't mean they should paralyze themselves out of asking others out, be afraid to initiate at all, or live under the tyranny of some ridiculous fear that if they so much as a approach a woman it will yield a lawsuit.