As the weather turns colder, we hear more and more appeals to give. Whether it’s because the frigid winds make life harder for people, because the religious holidays inspire us to give, or because ’tis the season to get your last tax-deductible donation in – we are asked more and more to give.

It makes me wonder – what’s the right way to give? Earlier this year, there were two women standing outside my church  holding signs indicating they needed money. Sure, I’m used to getting hit up for money when out on the town, but seldom at my neighborhood church. But you have to give them credit; it was a good strategy to either catch people who believe in seeing Jesus in the “least of my people” or make them feel guilty by walking by.

That sight in my own backyard made me wonder: What is the right answer to panhandling? And I’m not saying there’s a universal answer, I’m asking what is the right answer for ME to blend my thoughts on God, economic development, social justice, and everything else that goes into it when I hand over that dollar on the corner or the check in the envelope. DDN pal Amelia Robinson got all sorts of flak for sharing her perspective, so obviously this is something that many of us have an opinion on. So, I modestly offer my personal crisis of conscience and invite you to share  –  What do you do – and why?

So, here’s my journey…

Thought One: If I can help by offering a few bucks, I should. If I’ve done a good thing to help another human being, I can rest easy knowing that I was generous with good intentions. Anyway, it’s not my responsibility if they use it for drugs, alcohol or other vices.

Thought Two: I should focus on the “teach a man to fish” theory and say “no” when I’m individually asked. That way I can make my donations to the social services that are working to support the many people who struggle and I don’t encourage more panhandling in the city.

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Songs like “Mr. Wendal” by Arrested Development (thanks for that throwback, Slacker) simplify and beautify giving to people on the street. And Carlos from Living Philanthropic demonstrates a lot of great ways to give – like this recent FB post where he shared, “I met a very pleasant woman without a home today who was casually complimenting people walking by. I loved how much positive energy she was sending out into the world, so I shared my lunch with her and gave her some money. It’s the little joys in life.” So – giving on the street helps people and makes us feel better, but as romantic as those versions are, I’m not convinced it’s the RIGHT thing. Is giving really that complicated? Should we second-guess ourselves so much and worry about how our dollar will make the biggest impact or should we just see a need and help out a bit? I don’t know, so I’m passing the buck. I reached out to some people who are much more likely to have an educated opinion.

Up first – the religious spin.

Like I said, this article was inspired when people asked for money outside my church, so first stop – I talked to my priest, Fr. Dan Meyer at Holy Angels. He shared his experience with me of how he handles situations when approached for help. Often times, people in need will walk right up to the door of the church or the office and ask for money for food, gas and other necessities. Fr. Dan will personally purchase food or other necessities (it’s a short walk to Arby’s and Speedway), but if the push is just to hand over some dollars, he connects those in need to the agencies that can help.

But what about me – is that what he thinks I should do? Unfortunately, the Catholics are getting away from some of the “top down” mentality of telling people right and wrong in every case. He pulled out the “informed conscience” theory and instructed me to pray on it, know what the church teaches, get good advice, and make my own informed decision and see how I feel about it. Dang. No answer.

But he did leave me with the reminder that “Jesus told us that we will ‘always have the poor’ with us. We’re called as a church to help, but sometimes we have to set limits. We do what we can do.” My take-away: It’s my obligation to do SOMETHING, but it’s okay if I can’t give every time I’m asked or if I make a decision to support in other ways. Like Fr. Dan said, we do what we can do – and that’s our choice to decide what is ‘enough.’ But I can’t shake that we’re supposed to help the less fortunate. My quest continues…

David Spinrad, Rabbinic Intern at Temple Israel offered some powerful insights blending scriptural study and personal experience. He shared a quote from the Talmud that explains a biblical verse on giving as “If the choice lies between a Jew and a non-Jew, the Jew has preference. If the choice is between the poor or the rich, the poor takes precedence. If the choice is between poor who are our relatives and the poor who are strangers of the town, poor relatives take precedence. If the choice is between the poor of our town and the poor of another town, the poor of our town take precedence.”

Not being Jewish, you might ask what this has to do with me. Well – it offers a nice structure. Spinrad believes this teaching can be explained as “trying to establish concentric circles in our spheres of obligation. Never are we free to ignore the needs of others, but it is appropriate for us to establish priorities that extend from inward to outward.” Okay – I can get behind that. I’m an autonomous person and I have the right to give to people I know and causes that are close to my heart and my community. It’s my money – I can decide what I want to give to. But does that make me blind to problems beyond my personal experiences? If we all only gave to those within our church, family or neighborhood are we neglecting people in deep need that we aren’t affiliated with?

Beyond the scriptural teaching, Spinrad also pointed out how he acts in everyday life, saying “Our monies are better spent giving to lean, well-run organizations that are adept at getting help and services to those in need. I do occasionally give money to people on the street, but I have no illusions when I give it: I understand the dynamic between giver and receiver in that situation to be one of manipulation. No lasting good is done. I simply make myself feel better in the moment and reinforce the situation. Still, to turn a blind eye is a pain that leaves me feeling such remorse. And yet, I resent that this is exactly the emotional manipulation in which I am participating.”

So from both religious leaders, I received an acknowledgement that even though we come with best intentions, we may be making a systemic problem worse by giving on the street. But sometimes that makes us feel just a little bit better that we ‘helped’ someone. What a challenging paradox!

Tomorrow in part two of this column, I talk to individuals who deal with panhandling and homelessness on a daily basis and I determine how I react when approached. Until then – what influences your decisions when you’re hit up for money? Is it about religion, economic development, or personal responsibility?