So I’m really not comfortable making the first move. But as a non-binary male, I’ve come to accept that someone has to, and in all likelihood, it’s going to have to be me. What stops me from doing so are the fears born from talking to friends who are women, and hearing lots of venting about people who approach them when it’s not welcomed.

As a personal principle, I’d never approach someone while they’re at work (maybe unless I am on *very* familiar terms with them). But I don’t seem to see a lot of agreement beyond that. If you’re out with friends, would you rather be left alone? Responses vary. How about when you’re just doing a hobby you enjoy? Again, responses vary.
The rules just seem very inconsistent, and up to the whims of the moment. Which is understandable to me, but I hear a lot of flak given to people who approach at inappropriate times or places when I don’t always see what the problem is. But I REALLY don’t want to be the reason someone has to vent to their friend later. So I’d like some honest input on what the ideal time, place and circumstances would be?

Additional context since I know it helps:
I shower daily, hair and body wash included. I dress okay, but nothing to write home about. Usually comfortable sweaters and clean pants. Looks probably depend on taste. If I presented differently, I might even be conventionally attractive. But I don’t, nor do I intend to. So I think most people would agree that I’m just sort of attractive, but not pursuit worthy. I’m also a little socially awkward, but really, that only comes out as a sense of apprehension when initiating conversation. Once an actual conversation starts, I’m a pretty decent conversationalist. Lastly, I am seeking something genuine. I’m not exactly asking for a relationship from just anyone I spot in public, but I’m not just out for sex either.
If there’s anything I missed, feel free to ask.