I don't really work in a dangerous part of town. But there's a group of shiftless young men who constantly pop up here and there. I refer to them as the Meth Head Bicycle Club (MHBC) as they tend to bike around and assemble in small groups at the local McDonald's or Rite-Aid (where AFAICT they take turns shoplifting petty items).
The other day I was walking to a nearby restaurant in the area that takes me along a somewhat marginal low-traffic area that borders an older industrial zone. As I'm walking down the road I see a member of what looks like the MHBC biking towards me. As he got closer, I noticed he was audibly muttering random swear words. I didn't feel threatened by it but was obviously on my guard. He biked past without incident and I just concluded he was crazy. But something didn't seem right about that conclusion. Why the bike (which was one of those urban lowrider types and seemed to be in pretty good shape)?
Your first bullet point now makes me wonder if this wasn't actually a quite uncrazy deliberate behavior. That would make more sense.
They either will ask for money again, if you're lucky, or if you're not, get angry and then you're in a confrontation with somebody who has a lot less to lose in a fight than you.
I would recommend against anyone doing this. The best thing to do is keep your mouth shut and walk away.
Sure on an intellectual level, everyone is a human being, deserves to be heard, not feared, etc, etc.
At night, in a neighborhood ridden with crime, seeing a bunch of teenagers zoom on your from across the street and starting to cross the street toward you, it is easy to re-assess some priorities.
If you look like you'll bolt the moment you're threatened, that's a better outcome. Better than being stabbed or shot, at least.
* walk quickly, don't look lost
* keep your head up
* brief eye contact with people you see/pass
but honestly, 99% of not being accosted is being male, so it's impossible to tell what really works.
In situations like this, if there is an aggressor (say the customer in this case) they expect a certain outcome. They envision how the interaction will go. "I'll be demanding. Employee will get upset, maybe a bit snippy. I'll yell at them and show them who's boss. Maybe even complain to the manager." But in turn they see a smile, complements ("Oh, what a beautiful Porsche you have!") and willingness to help. They are angry inside but it is hard to manifest it without appearing completely crazy.
I've heard of other stuff like this:
* In a dangerous part of town and see a bunch of shady people eye you up -- act crazy, mutter to yourself and maybe flail your arms. Friend liked to do this in a bad part of Chicago.
* Someone wants to pick an argument and is just contrarian no matter what you say. At first argue a bit, then immediately switch sides and argue against your old position (basically on their side). Also to make it fun, be kind of aggressive and angry at your old position just like they were.
* An aggressive panhandler is verbally harassing you asking for money. "No thanks, I'm good. Talk to you on Wednesday". Say it, as matter of fact as possible. Their mind will stop for a bit trying to process that, and it gives you enough time to walk away far enough.