Photo by Emily Morter on Unsplash

A few years ago, a desperate-looking 50-something-year-old guy flagged me down on Michigan Avenue, asking for my help.

He wasn’t homeless (at least he didn’t look it). He was well-dressed, well-groomed, and was frantically talking to someone in his bluetooth headset.

He explained that he’d just been discharged from the hospital and didn’t have the cash to buy a train ticket back to the suburbs, where his ailing mother lived. According to him, he’d lost his wallet at the hospital. He just needed $15 for the train ticket.

Much like Dumbledore, I have the simultaneous strength and weakness of having a lot of trust in people.

The story was… questionable, but he looked to be in so much distress; and my brain couldn’t compute why a well-dressed guy with a bluetooth headset would be trying to fleece me. I mean, he even offered to pay me back later. And his ailing mother was on the other line, saying she needed him home.

So, being the trusting person I am — and just generally overstimulated by the whole set of circumstances — I gave him the $20 bill in my wallet. He tearfully shook my hand and offered many thank yous for my help.

Two weeks later, walking down Michigan Avenue again, I was approached by the same guy — bluetooth headset and all — asking if I could help him out. See, he’d just been discharged from the hospital…

After his same spiel, I angrily (both at him and myself) said, “Don’t you remember me? I gave you $20 like two weeks ago.”

Then he just walked away. Probably to go ask someone else.

I’ve always been trusting of people, institutions, and life in general.

But over the past few years, I’ve begun to seriously question that trust.

Sure, the 2016 election blah blah blah.

But I’ve also started questioning my trust with personal life stuff.

Doctors have made mistakes with me. These authority figures who I’ve always put so much blind trust in. Now I get super skeptical when they recommend something and ask TONS of questions. (Which you should be doing too! You’re your own best advocate!)

Pay raises were promised and never materialized.

Friends said they’d still make time for me after they started dating someone or got a new job, only to never reach out anymore.

There’s the Starbucks order that was supposed to be an UNSWEETENED iced coffee, not the SWEETENED one I got!

If you can’t trust that your coffee order will come out right, what CAN you trust, you know?

The answer, of course, is partially found in the proverb: “Trust in God but tie your camel.”

But also, like, you can’t really trust anyone or anything. That’s the hard truth I’m starting to come to terms with. (Yes I am 33 and should have realized this waaaay earlier, but better late then never.)

Having a skeptical lens on everything feels weird.

It feels negative and pessimistic. But I’m also learning that it’s about survival. It’s about accepting that people are mostly good but you also gotta be on your shit and protect your neck in this life.

It means setting up stronger boundaries, being less “nice”, and saying “no” without feeling guilty about it. (As a recovering people pleaser, this is all very new territory for me!)

That said, I’m not some cold-hearted robot either. I still trust that The Great British Baking Show is pure and innocent. (Hey, call me naive.)

It’s just about being more cognizant that there’s a grey area between “trust” and the fact that life can’t entirely be trusted.

As I type this on my laptop, I’m sitting in a coffee shop in Chicago. And I really need to use the bathroom.

The person next to me seems trusting enough. They’re using a Macbook too and have a copy of the Wall Street Journal next to them.

If I ask them, can I trust that they’ll watch my stuff while I go use the bathroom?

I hope my stuff’s still here when I get back.

I write comedy things. the ha & lol. Also a founding editor of Slackjaw on Medium.

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