I share the concern that by handing some of these people money, I might be providing their next fix and perpetuating an addiction. It's happened at least once: in college, while waiting for a friend at a train station, a woman came up to me and said she was almost out of gas and she just needed a few dollars to be able to get home. I gave her whatever bill I had in my wallet. After my friend emerged and we were on our way, he mentioned one of the employees inside warned him about a woman who hangs around at night asking for gas money, which she does not spend on gas. I fumed a bit.
And yet, I am never comfortable passing those people by. I do it rather frequently. But it's never a good feeling.
One of my little siblings' godmother (were the type of family where you eventually lose track of who exactly is godparenting who) says, "What I do with my money is between me and God. What they do with it is between them and God."
And today I read this article -- which is great on several levels -- that includes this line:
Jesus didn't say, "Feed the deserving." He just said, "Feed the hungry."