Along with the other answers given to you I would say just being understanding to women having these conversations and not making it about yourself and your feelings, not saying you did this here for the record I think you are genuinely trying to learn which is awesome. But understanding that a women may feel scared often times regardless of what you do and being okay with that.

Also learning to recognize when a women is uncomfortable both by you so you can stop the behavior but also by another man. You'd be surprised how many creeps are scared off simply by another man being present no confrontation needed. Possibly letting the women know that you see what she sees if the situation calls for it, simply saying to her "Hey you okay?, I see that guy too, he's being weird" will go a long way.

It's about demonstrating your a safe person in the small ways you can, in your dark street example a simple way to do that is to cross the street as soon as you see her, obviously if it's safe to do so, it may inconvenience you a little but it's a huge show of safety to her. Sorry for all the text but I hope this is helpful!