I’m gonna have to say in the current social context it’s almost never acceptable. Post COVID people are only sticking with their already made friendship groups. There are laws being introduced soon that will make “street harassment” illegal and that is subjective i.e. he made me feel threatened (when you were actually trying to be loving). The rise of trans and queer rights is great and I’m all for it but most women will just say that they are in a relationship already or say they are gay these days as a way of telling you to fuck off without actually saying that. I’ve interacted with lovely women and messaged them the day after asking how they are and they’ve literally blocked me for no reason. Unless you’re a billionaire it’s almost impossible to get a date these days! If you’re one of those people with school friends who you still speak to maybe try and get introduced by someone who knows you to someone who already likes you that they know.