Oh, do I have beggar stories.
With the exception of my solo trip to Las Vegas a year and a half ago, I don't hand out cash any more. ( I was just in a really happy and generous mood. Vegas will do that to you).
One late night at a gas station just outside of Detroit, a 30-something woman pulled up to a pump while I was putting gas in my car. She claimed to be pregnant, that her boyfriend kicked her out, and she needed gas to get to her parents' house. I suspected she might have been full of crap, but I offered to put $5 in her tank. I walked into the store and paid the clerk $5 for the pump where she parked. As I was walking out, she walked in and said "I wonder if they have a bathroom here." What she really did was ask the clerk for the $5. He said no, that she had to put the gas in her car. I learned this because I went back in to buy a drink, and the clerk says she does this all the time.
Another time, at a nearby gas station, there was a disheveled looking man holding a 2 gallon gas can loitering in the lot. He asked for a few bucks so he could buy gas, and I gave it to him. He didn't even wait until I left; he started asking other people for a few bucks for gas, within clear earshot of me.
This third one is a bit different. Bright sunny day, probably 70 degrees out. I had just parked my truck at a local grocery store. Within seconds of exiting my truck, a man drove up to me on an electric scooter, quickly enough that it caught me off guard. I ordered him to stop and moved my hand near my concealed pistol. He looked to be in his 40s and seemed to be quite able-bodied. He then told me the battery was dead on his scooter (clearly it was not) and that he needed a ride two miles to his house. He could have easily walked it home. I declined and went on my way.
A long time ago, in a galaxy far, far away, I worked as a valet. The company I worked for had several accounts, including one where nobody ever wanted to work: The Pretty Woman at 7 mile and Van Dyke in Detroit. It was bad. All evening, I'd have people walking by trying to sell drugs or stolen merchandise. Fortunately, I rarely got stuck working there. So this big black dude came walking by, trying to get me to give him a dollar. He was clearly high on something. After refusing him several times, he said "I tell you what. You just give it to me to hold on to, and when my white woman comes to pick me up across the street, I'll give it back."
