I was with you (to a degree)until:

they’re supposed to miraculously become an expert in navigating a potentially life-destroying minefield, where the only two outcomes is magically getting it right, or risking a non-trivial probability of incarceration and a criminal record when they (invariably) get it wrong?

This is some nonsense. The worst the man will get (barring some VERY unacceptable behavior on his part) is yelled at by an angry (and probably shitty, if all the man did was politely approach at even a remotely reasonable time) woman. Which, turns out, is something women deal with from shitty men fairly regularly. It turns out, when you are interacting with strangers out in public, there is a small chance you are going to interact with an asshole. That doesn’t mean you should be a hermit, that means you met an asshole. And if everyone you meet is an asshole… you’re probably the asshole.

But nobody is going to jail or having life-shattering consequences for saying hello to a woman they don’t know.

THAT BEING SAID, if we, as men, are regularly told that approaching a woman in public is uncomfortable, unpleasant, or downright scary for women, decent men won’t want to approach women in order to avoid making them uncomfortable.

My personal experience has been to the contrary, and have struck up conversations with a number of women I didn’t know in public, and never had a particularly bad experience. Maybe I am generally non-threatening, or maybe I have better social skills than some, but if all a person who rarely interacts with women hears is that initiating any sort of contact is unpleasant to the woman they talk to, I can’t imagine they’d be inclined to strike up a conversation. And if they do make women uncomfortable (due to poor social skills from… not regularly interacting with women), it only reinforces that belief.

What’s the answer? I don’t know. But it feels like making men who care about the feelings of women uncomfortable with approaching them does nothing but leave the ones who don’t care. I think the message needs to change.