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…
