Yeah, if you clearly and calmly signal your needs before you get too close then sure, no judgment, neighbors helping neighbors and whatnot. Hell, a guy just giving the head nod then staying on his way makes me feel a fair bit safer because he’s communicated “I see you’re there and that you see me”. I’m still afraid because he could be lying about his intentions, but I can keep my distance a bit, stay on alert, and have my hand on my pepper spray while I explain that I have no idea where anything but the transit stop/station is.

The rich guy in the example on the other hand, what the hell does he want from me?

And hell, I distrust a large group of people coming up to me regardless of gender as well as anyone trying to get my attention from a car.