I am generally cautious about engaging people directly, I'll admit. I...was not always this way. In Oklahoma I did my best several times to befriend and serve. I was used and conned a few times by strangers...frightened even by a couple of guys who figured out where I lived. Came to Chicago and was immediately conned. Hah! Naive little farm boy that I was... I suppose I needed to learn that one really doesn't let strangers into their apartment building.
Was actually a "social worker" for a few months in Oklahoma...the only job from which I was ever fired. It was a small community action agency that dispensed emergency food and utility assistance among other things. I'm just a bit too sensitive to actually survive as a social worker, though. When I wasn't being conned (hah!) by the folks who came into my office, I was hiding in the pantry weeping. Alas! That was some bad three months, let me tell you.
Here in Chicago, there are plenty of people on the street where I live asking for money. If I give to them, I find it is best to not listen or think too much while I do. Everytime I've listened to their stories, I realized afterwards that they were lying to me. Not that it changes anything...they obviously had some need. I simply prefer to not give them the opportunity to be dishonest...no need to mix a lie (and my judgment) into our brief interactions. Like Daniel, I try to look everyone in the eye, and smile even if I do not share. I find that they do not respond well to any apologies on my part for not having anything to give...a small window, I guess, into the shame of begging. There is always a certain amount of pain when I do not give...and sometimes a very great deal.
I feel most comfortable giving to organizations. My current pet charity is the Chicago Food Bank. I hope that when I give, it is used well, but one never really knows. Giving is somehow deeply shaming to me, and I hurry away from every act of "generosity." Truth is...it's hard to think of myself as being very generous, but I'm trying to learn.