Because they've been messaged their entire lives that doing that is not what men like or want - and norms around dating are the stickiest ones - changing at a slower pace than others. Slut-shaming plays into this as well, and you've completely and entirely discounted that when you're literally treated as prey in this culture, that safety elements are a huge factor. Date rape accounts for about 85% of rapes. Is he going to think that I'm easy and "want it" if I approach him first?

We can certainly support people transcending their socialization and we absolutely should, but you don't seem to appreciate that dating is just as fraught and nerve-wracking for women, albeit in slightly different ways. It's an incel lie that women are just happily waiting to pick from their many suitors.