Panhandlers and the Sermon n the Mount

This morning I had missed my bus to work and needed to transfer at a stop at a major intersection. This part of town is not known for crime or poverty, but what happened shows that it is everywhere.

A man came up to the bus stop (I was the only one there). He was short, gray haired, about 50ish, rough whiskered, and looked homeless.

Him: "Do you have a quarter to spare?"

Me: "No, I don't." (I don't...not to give to people before I know if they are honest)

He sits down on the bench under the shelter, and several minutes pass. By this time, the clouds are getting dark and it starts to rain and lightning.

Me: "Where are you going?"

Him: "Fourth and Magnolia"

Bus 25 was about to arrive any minute, and it went several blocks from there.

Me: "Well, if you need the quarter, get on the bus and pay your 75 cents and I will pay 25 cents. It's not that I don't want to help someone, it is that I wish to be wise."

Him: "Well, I actually like it here in St. Matthews. I've enjoyed my time here. Bye."

And he jaywalks across the street.

Now, several things were going through my mind. First, how can I be truly helpful to this man and be a wise steward with the money God has given me? Second, is this man wanting money for his next drug fix (or lazy and won't work), or is he really in need of money? Thirdly, how could I as a woman properly deal with this situation? There were lots of cars on the road, so I did not feel too much in danger, but I wanted to be cautious.

My guess is that he was a panhandler, as he turned down the bus ride. I know that this is the wise way to do it in other situations: if someone wants food, don't give them money. Instead, take them to a nearby restaurant and buy them something. Also, I have heard to be careful what grocery you take them to, as they can return the food for cash (Kroger is a safe one to go to, if I recall correctly).

I would love to hear your stories and how you deal with these issues. What would you have done?