08/23/2012 07:49 am ET Updated Oct 23, 2012

Can You Spare the Bread? Should You?

My wife and I recently moved from a village in Vermont to Evanston, Ill. We now live in a diverse neighborhood, half a mile north of the Chicago city line, and we're enjoying it. We deliberately wanted to trade idyllic beauty for the energy and opportunities of a real city.

Here in Evanston, homelessness and poverty are on the street corners. In Vermont, these things exist, to be sure, but they are tucked away and usually fairly quiet.

I have been asked for spare change, directly and indirectly (the poor holding signs at street corners), dozens of times over the last six weeks. The only one that I responded quickly and easily to was a man named Solomon who rode up on his bike one day as we were walking the dog, and asked if we knew of a nearby shelter. We were new in town. We didn't. "Can you help me get some food?" Solomon asked. And then, we were all over it. We didn't hesitate in walking with Solomon to the nearby Subway and buying him a footlong. But that experience was atypical. The encounters are hardly ever that clear, nor the answers that simple.

A decade ago, when my older kids were young, I would hand them each a roll of quarters when we were visiting New York City, instructing them to give to anyone who asked. Of course, I know very well the potential problems with such an approach. I know that some of the poor are working for others almost as indentured servants, and that those quarters don't end up in their pockets or translate into food in their stomachs. And I know that some of the homeless are addicts and that their needs are not solved, but are probably exacerbated, by quarters. But I decided to err on the side of unquestioning response to those in need. Nevertheless, to do this now, no longer feels entirely responsible.

Then, this past Saturday, we went to synagogue, and a text from Deuteronomy 15 felt like it was speaking directly to me. Here is a condensed version of verses 7-11:

"If there is a needy person among you, do not harden your heart and shut your hand against him. You must open your hand and lend him whatever he needs. Beware lest you think to yourself, he will find help elsewhere, and give him nothing, for he will cry out to the Lord against you and you will be guilty. Give readily and have no regrets. There will never cease to be needy ones in your land."

So I posted on Facebook Sunday morning: "We are trying to figure this out: How to respond to the homeless/poor on the street without, on the one hand, handing out cash and coin, and on the other, not shaming them further by taking them by the hand to buy food or ask how they'll use the money etc. Any suggestions on how to navigate these two extremes are most welcome!"

One friend commented, "Build a house," and I would love to do that, if I could. I honestly think that I would. But in the meantime, how should I respond to the faces on the street in need that I see every day? The comments poured in.

"Write a letter to your legislators asking them to ensure that the poor get what they need," frankly wasn't very helpful.

Another friend wrote, "Volunteer a few hours a week at a neighborhood food or clothing bank," which is obviously a fine idea but sort of beside the point I was making and the personal problem that I was trying to solve. I am not interested in simply alleviating my guilt for having more than others; I want to know how to give freely and respond ethically, given the complications of doing so in our day and age.

A friend with lots of experience working in religious organizations in Boston wrote this: "When I worked on Beacon Hill and walked up to the office from South Station each day, I gave myself a weekly budget that I would simply give away, no questions asked, no 'deserving' required. Then I prayed for a nudge from God about who would get it. Not everybody's answer, but it was mine." That was my approach with my older kids, years ago.

"I worked with a homeless organization in Berkeley for awhile, and one thing you can do is look them in the eye and acknowledge that they exist," was a no-brainer, for sure, and yet, it can be difficult to do that when you are not prepared to follow-up the acknowledgement with an actual gift.

And then I think we got to the crux of it, to solutions that will work.

"Gift cards to local fast food places or convenience stores. A $5 gift card to Subway gets a footlong sandwich. Also, I have a rule that I always give to homeless women," wrote a friend from Cleveland. This is what we did with Solomon that day on the street.

"I give out gift cards to fast food restaurants and I keep a stack in the car so I am prepared whenever I see the need," echoed another friend. And then some friends commented that fast food restaurants are part of the problem and perhaps not the best solution. But again, that seems beside the point.

"Carry small care packages -- non-perishables like granola bars, water, toiletries, that you can easily give. And if you give money, give without judgment," wrote a friend. Yes, but am I really going to carry such things on my bike, which is my usual form of transportation?

For now, as of today, I am walking to Subway and stocking up on gift cards. Our response to Solomon that day on the street seems like the best immediate solution to the problem. The only thing I would do differently, today, is invite Solomon to come around more often. Still, if you have better ideas, I would love to hear them.