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There is a man who often sits outside my local supermarket asking for money. When I go shopping, every week or so, I typically try to give him a dollar or two, but I’d really prefer to give him food instead. But if I ask him on my way in what he wants to eat, then sometimes he’s not there when I come outside with the thing he’s requested. Sometimes that’s just annoying to me, sometimes I’ve purchased a non-kosher item at his request that then I’m not going to bring home, and sometimes I just feel like I’ve missed the opportunity to help him. But also, sometimes, if I give him a dollar on my way in, he asks me for more money on my way out. What’s the best way to be a good person without getting stuck like this?
You are obviously a very good person to give this much thought to another human being in need. While I realize you’re not in this for the external reinforcement, I want you to take a moment to sit with the fact that you’re already doing more for this person than probably 95 percent of the people walking in and out of that store. While it would be best if our society took care of the most vulnerable among us, in a world where there are unhoused people with significant needs, what you’re doing is beautiful, and also what you’re doing is not the make or break situation for this person. So, first of all, cut yourself some slack.
My personal recommendation is to give money on your way in while making eye contact and saying hello. This direct and personal interaction may decrease the likelihood that he’ll ask you again on your way out. It may not, though, in which case you can be prepared to say something like, “I gave you all my ones on my way in. Have a good day and see you next time.” If this feels impossible to you, consider giving one dollar on the way in and keeping another dollar in your pocket for your way out if he’s still there.
In addition, if you want to buy some packaged snacks or some food of a variety he’s requested in the past but that you would also be happy to take home, you could put that on the top of your cart and offer a granola bar or something similar on your way out as well. This way, you haven’t missed the chance to perform an act of lovingkindness, but you’re also not saddling yourself with food that may go to waste, which feels antithetical to what you’re trying to accomplish.
Even if you want to take food requests, it’s appropriate to have boundaries. You don’t need to buy food that may go to waste, either because it’s not kosher or because you just wouldn’t use it if you can’t give it away. I also want you to dig in a bit to why you prefer giving food to giving money. I know there are lots of opinions about the “right” way to help, but don’t assume that you know that a sandwich is overall more beneficial than a dollar.
Finally, I want to encourage you to get involved with organizations where you live that address homelessness and food insecurity. What you’re doing for this one person is valuable, but it’s also not going to address the reason he’s living like this or solve his long-term issues. Working on a systemic level – or at least finding out what other advocates are doing on a larger scale – could give you some resources for supporting this person and other people you encounter on the street and may help you channel your desire to help.