Yesterday on the way back home I came across a rough-looking guy. Sweating, dirty, walking with a cane. When he started talking to me I stopped. He told me he was from Metairie, and then told me he had diabetes and something else wrong that I didn’t really hear because I wasn’t really listening. He asked me for some money to help him out and I said “sorry” and walked away.
Then he said, “F*** you, man.” I kept walking as he continued to rant, but I could still hear it and eventually I was so pissed I turned and said something not very nice, and then went on my way, now fuming to myself about what a jerk he was. Then I went into a store and perused shelves of high-end imported Belgian ales to bring to a dinner party. And now we’re firmly in “Man Struggles With Affluence/Guilt” territory. But it’s more complicated than that, right?
I left the store and started to look for this guy. I spiraled out and did loops around town, trying to track him down. After a while, when I’d pretty much given up and was headed home, I saw him again. I walked up, told him I was sorry about our last exchange and I handed him a bill. He gave me a handshake. He explained his story again in more detail, but I mostly didn’t listen this time, either. I told him I had some family back in Louisiana near him. He told me he understood why it’s so hard to trust someone asking for a handout. We shared a fist bump and we went our separate ways. It was hot and I wanted to go home. I realized walking back that I hoped I didn’t see him again. I’m not sure how to feel about that. And I’m not sure, never been sure, whether I should give or just move on. If I gave to every beggar that asked me, worst case scenario? We’re talking like $100/year, maybe. But still you wonder if it does any good, but then again does it really matter because it doesn’t affect me that much, anyway, and then you start spiraling out again. There’s never an easy answer, which is both depressing and a kind of relief. It’s nice to have something unsettle you every now and then.
Mark Larson 
I wonder how much of your initial hesitation to give stems from a sense that generosity in that context seems ineffectual. If you believed that your change, perhaps combined with other people’s change, might actually make a longer-term difference, it wouldn’t be so hard to give, right?I struggle with the whole phenomenon, as well. I end up being torn between resent and pity and neither is a good place for charity to start.