The Guilt Of Not Giving To The Homeless

The Guilt Of Not Giving To The Homeless

If you live in a big city like Chicago you’re likely to see a homeless person every few blocks.  They’re on street corners, under bridges, or on trains and buses. A lot of times they’ll be looking for donations hoping to pay for a place to stay for a night or to buy some food.

Sometimes you’ll reach into your pocket and give a buck or two…or some change.Yeah, me too. Sometimes you’ll just walk past. You might be in a hurry or maybe you just don’t feel like giving that day. Yeah, me too.

Do you feel guilty when you blow on past someone in need? Maybe a little? Yeah, me too…well I did but I’m getting over it.

My story is probably a little different than yours. I lived in a shelter for more than a year. Although I was never on the street asking for money, I can relate. I understand their story and their predicament.

When I left the shelter last February, I was an easy touch. I gave a little something to almost everyone. A buck here. Some change there. These were my peeps. I was happy to help.

At first I would talk to someone as well as giving money. One night in Los Angeles, I gave a man $2 and mentioned I was just out of a Chicago shelter. We exchanged life experiences. Shelter living vs street life. I knew I was going to use our talk to write about homelessness in LA, so maybe this wasn’t the most selfless act of my life but he got two bucks and I got a story. Win/Win, I guess.

So back to this guilt thing….

After a while I stopped giving cash to everyone. Hey, it gets expensive. A buck here, a two spot there. I don’t want to have to get a job to give money away. I felt kind of bad and would always say “Sorry, not today but good luck. I wish you well.”  I still do that.

The bad feeling stopped last week.

The photo at the top is a Streetwise. It’s a newspaper about homelessness sold by the homeless. Last week I wanted one and found a guy selling them at my local Walgreens…at least that’s what I thought.

When I tried to buy one, he said the papers in his hands weren’t Streetwise and he promised to have them the next day. I gave him a buck anyway. When I came back the next day it was the same thing. He was pretending to sell Streetwise to make it look like he was working to make money.

A Streetwise scam! How fucking disillusioning

I’ve seen him at the same location every day since then and not once have I been tempted to give any money…and I don’t feel any guilt at all. Not one drop!

But this is the incident that broke my guilt cherry. I’m walking out of a donut shop and see a man sitting in an alley with a cup. He asked for some money and since my smallest bill was a ten and my change went in the shop tip jar, I said sorry and wished him luck. His response, “Hey asshole, you don’t have a fucking dime?”

I’m pretty sure Sales 101 says you don’t close the deal by calling your customer an asshole.

So have these two incidents left me jaded and sour? Not really…okay maybe a little. I still feel empathy for their plight and help when I can. I’ll still give money when I want and not feel bad about it when I don’t.

But I’m still looking for a Streetwise. Anyone know where I can buy one? Sigh!


This has been the latest in the Faces Of Homelessness series. Click the link to check out other pieces.

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