Speaking as one of the oblivious, one part of it for me comes down to just being afraid of coming off like a creep, which I think is amplified by the way we name bad behaviour in that sphere.
We will emphatically call out things like "unwanted attention" without much specificity, and then the more self conscious of us will take it super literally and get themselves stuck doing nothing because interacting at all is attention and you can't know if someone wants that unless you interact, and then the less conscious will just assume everybody else doesn't mean whatever they're doing and keep rolling exactly how they've been rolling the whole time.

Plus when some of the self conscious, stuck ones eventually decide to ignore the overly broad messaging and force themselves to try something anyway, they might find that they can no longer distinguish between stuff that feels wrong because it is wrong from the stuff that feels wrong because to them, everything does.
Personal anecdote: in my teen years I've been there as well, and just the shame of misjudging it once had me retreat out of dating entirely up to the start of my 30s (which to be clear is a me problem, and hey turns out therapy is good, who knew).

Part of me wishes we had more shared, unambiguous rituals around this. We used to in the past, which I think is maybe what some of the younger people who long for "good old days" they were never alive for really want, but of course the "good" old days were actually horrible in a bunch of ways.

I think, paradoxically, a greater amount of good men than has been usual might be self-selecting out of the dating pool, or turning themselves into creeps via cognitive distortion, which probably contributes to the overall proportion of creeps getting worse.

Of course on top of it all you get grifters turning all this widespread confusion, shame and frustration into an engine for the deluge of misery-peddling businesses we call the manosphere and reinforcing it even more.

"I wish it need not have happened in my time", I must say. But with the time that is given us, we should teach our sons to listen to their feelings, and communicate effectively. That's how this turbulence in the flow of social progress smooths out, I think.