I gave a homeless guy two bucks recently. He was older, with gray unkempt hair, oversized clothing, a week’s worth of stubble and no teeth. He saw the Starbucks cup in my hand and said in a rough but friendly voice, “Nice morning for a cup of coffee, isn’t it?”

He had no idea the odds that were against him when he first approached me.

 For a long time, I’ve had a policy against giving homeless people any sort of help. I’d heard that it’s more compassionate; there are shelters and services where they can go for a meal, a cup of coffee and help. Giving money discourages that. But if I’m being honest? They make me uncomfortable. I wonder about their disposition, their mental condition, if they’re high on drugs or blotto on alcohol. If they ask me for money, I’m suspicious of their intent, and say sorry, no. Routinely, I avoid eye contact. I look right past them.

But recently, I saw something I couldn’t look past. As I waited for a red light on my way home, a disheveled one-legged homeless woman was attempting to roll her wheelchair up a small hill where Greenback Lane approaches the I-80 overcrossing. She wasn’t succeeding. As I sat across the street from her, in the air-conditioned cab of my truck on a hot June day, I watched her struggle to move even just a few feet. At one point, she turned her chair around and with her one leg began pushing herself backwards up the incline, about six inches at a time. Her face was visibly red. She was sweating.

My light turned green and I thought, I should pull over and help her; park my truck, get out of my comfortable cab—and my comfort zone—and help her. She wasn’t pestering me for change; she obviously needed a hand. I even slowed as I passed her to get on the entrance ramp. 

But in an instant, all those usual thoughts flashed in my head: What if she doesn’t want help? What if she’s crazy? Or drunk? Or filthy? 

I kept driving. And I haven’t been able to stop thinking about it since.

How numb have I become to the troubles of others? How did I get so indifferent to the suffering of those I’m uncomfortable with? I talk a good game about compassion and empathy, but I flat-out failed a test that was literally right in front of me.  

My broadcast partner, Pat Still, has an 18-year-old son, Dimitri, who has autism. Pat’s worst nightmare has always been that somehow, someday, Dimitri falls through the cracks and ends up on the street. I would help Dimitri in an instant now, if he needed it. But if I didn’t know Dimitri and was simply passing him on the street, would I help if he needed it…? I don’t like my answer.

I’m not naïve. I know some homeless are there because of poor or outright stupid choices in life. Some are criminals and cannot be trusted. But I also know that many are there through circumstances beyond their control: mental illness…physical disabilities…poverty…domestic violence. The list is long and sometimes complicated, and I don’t think it’s up to me to judge which is which. Not anymore. 

So yeah, I gave that homeless man two dollars, and maybe he got his coffee, or maybe I was duped. I don’t care. All I know is I’m going to try harder; I’m going to find a local shelter to support, because services are still the most important thing. But if I get hit up and have a spare buck? Screw it; they can have it. And if I see someone who makes me uncomfortable? So what. I’m done looking past them. 

Catch Tom on the Pat and Tom Morning Show on New Country 105.1, email him at [email protected], or follow him on Twitter @kncitom. Illustrations by David Norby.