That Time I Picked Up a Strange Man In a Prison Parking Lot

Spoiler Alert: I did not get murdered but I DID prove that compassion and goodwill never go out of style.

I’m not the one who ever gets wrapped up in politics. I prefer to be an ignorant Canadian with my head in the clouds where it’s nice and quiet and comfortable.

However, one would have to be dead to not have had some type of emotional reaction over what went down in American politics on February 28th.

I’ve always been the type who feels actual physical discomfort when underdogs struggle and lordy, did one Ukrainian underdog ever struggle last week.

Hence, my message today is one of compassion and goodwill. And yes, I can still squeeze this into our theme of Wildhood because this is such a wild (and feel-good) story!

All in the name of helping an underdog.

With the sheer number of people who go missing and turn up dead in ditches, this probably wasn’t the brightest thing I’ve ever done. I watch plenty of murder documentaries, I know how these stories go.

But, be nice or die trying, right? I feel like that’s a good motto…except the “die trying” part.

Is it naive to think that we can trust the average person with the way the world is currently? Or, is it necessary to give the benefit of the doubt in hopes that we are all good people on the inside?

For the most part, erring on the side of trust has been greatly rewarding for me. Let’s hope that trend continues because there are plenty of dark ditches out there just waiting for a body to roll in. 😂

I don’t know if most people would pull the stunt I’m about to share. In fact, I know I have friends who would read this and say, “Screw that!”

I have visited plenty of prisons in my day.

I recall a night after one of those visits when the universal gods of WTF called upon me to go above and beyond.

As I was leaving the local remand center, a man who had just been released from a weekend in lockup asked me for a really big favor. He asked me for a ride home. 😯

This remand center is located in the far northwest suburbs of the city. When they kick you out the door with nothing but a bus ticket, the nearest place to catch a bus is at the end of a long, dark walk down a country road.

The night in question also happened to be in the middle of winter.

Not my problem, right?

Right off the bat, I was baffled that this man thought for one second that a solo female would even entertain the idea of letting him into her car. Even more baffled when he told me where he lived, on the opposite end of the city.

Considering I live only a few minutes away from the remand center, it was a stretch for me to even consider.

He offered me sixty dollars for the ride and I knew a taxi to his end of town would cost much more. So, like Curious George, I decided to ask him WHY he was locked up in the first place.

I never laughed so hard when he told me.

He had a neighbor who consistently let her dog do its business in his yard, the same space his five-year-old child played. He repeatedly asked her to stop allowing the dog to do this for the sake of his child.

The lady with the dog continued letting her dog dump all over his yard, just to piss him off.

So, one night he’d had enough and he sought revenge. Under the cover of darkness, he peed all over her barbecue.

In the winter.

Then it froze.

Her surveillance camera caught the whole act and she called the police.

The man told me the arresting officer was so amused that he didn’t even want to make the arrest, but it was procedure and he had to do his job.

I was 100% convinced his story had to be true because who could make this up on the spot just to catch a ride?

After laughing myself silly, I invited the man into my car. We drove to the ATM at 7-Eleven, he bought me a cup of coffee, gave me the sixty dollars and his business card. We drove forty minutes across the city and I dropped him off at his very big and beautiful home.

Turns out he was the owner of a large contracting company. In hindsight, he likely could’ve easily afforded the taxi home but instead he chose to ask the lone woman. It’s almost like he chose human connection over the obvious solution.

I never did contact the man after that night but just as I’m telling this story, I’m willing to bet money that he has also told the story of the woman who had the guts to do a favor for a stranger in a prison parking lot.

Looking back over my life, I can’t help but shake my head at some of the risky choices I’ve made, however, trusting strangers has always worked out for me.

I will continue to look for the best in people and relentlessly stick up for the underdog because I believe it’s necessary (even if it’s a bit stupid). So far, no dark ditches have called my name.

Can we please fill the comments with more feel-good moments?

When was the last time you trusted a stranger and it worked out in the best possible way? Would you have asked what this guy’s story was? Would you have given him a ride?

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If you like the idea of talking to strangers, you’ll love this story…