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Q & R: Giving money to people on the street

Here's the Q:

First of all, thank you ever so much for your ministry, it has been a tremendous blessing to me.

I am writing cause I feel somewhat perplexed about a certain kind of situation regarding the poor. Sometimes when I am walking through the city, I encounter someone who is begging for money. I have to be honest, I sometimes feel baffled as to how I am to respond. Yet I feel compelled to respond, Im just not sure how. Every time I think about reaching into my wallet I usually think two thoughts. One, am I really helping this person by throwing a little money at the situation? Might I be doing this to simply make myself feel better? Two, I tell myself that I shouldn't give money to this person cause they might use it for drugs, alcohol, etc. Im not satisfied with either thoughts.

By the time I go between these questions I have long since walked by the individual, and I feel a bit awful that I didn't do anything. What do you think? How can I respond in Christ like way? I want with all my heart to "get on board" when it comes to Jesus message of helping the poor. Any insight you could give me would be much appreciated.

Here's the R:
First, God bless you for caring - and for monitoring the impact of giving, not giving, walking by, not walking by on your soul. I think all of us struggle with these situations.

Second, on the issue of motives, in Naked Spirituality, I quote David Steindl-Rast, who said, "Jokingly, but with a great deal of seriousness, [Father Damascus would] say, 'Don't worry about purifying your motives. Simply know that they aren't pure, and proceed.'"

But that bring us back to your question. What to do?
1. Some people try to carry some money around to give to people in need. They give, not because they believe their money will change the person's life, but simply as a discipline - because they don't like what happens to their soul when they walk by.
2. Some people buy some coupons/gift certificates from a local grocery store - to assure that the person will use the money for food, not booze or dope.
3. Some people don't give because they feel doing so is enabling people to remain in an unhealthy situation.
4. Some people do a little of each, depending on their mood, the situation, etc.
5. I imagine there are other options too -

I try to do 1, but if I've also wished I were organized enough to do #2, and sometimes I end up in #4. Whatever I do, I try to treat everyone as a human being - with a smile at least - whether they're a lawyer on their way to the court or a homeless person asking for coffee money. And if you meet a lot of needy folks, it's a great idea to find the ministries/organizations in the area that exist to help them ... and to support those groups generously, groups (in DC, for example, where I lived for most of my life) like Martha's Table and Georgetown Ministry Center, or in SW Florida (where I live now), like St. Matthew's House.
Check them out, and don't squelch a generous impulse!

I think it's important to respond to people in need, but it's also important to try to understand and address the systemic conditions that keep putting people in need. That's where books like Everything Must Change can be helpful ... and it's why movements like Occupy Wall St. have an important place.

I'd love to know - over on my Facebook page - how other folks respond to this important question.