We hear about online scams all the time, and like to think we're pretty wise to them.

When you're contacted by an old acquaintance on Facebook who's in desperate need of a $10,000 loan, you know it's fake. When a Nigerian prince wants to transfer his fortune to you but needs you to open a local account for him with some money in it, only a sap would believe it.

So when you meet a scammer in real life, you think you're so woke that they blindside you. My foolish confidence, it seems, is how I got tricked by somebody's heartfelt story.

It was late on a Friday afternoon and I was going out that evening, but didn't have time to get in with my regular barber for a quick cut. There's another barbershop within walking distance of my house so I quickly walked down before closing.

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I was greeted by a handsome, put-together, early 30s guy. He was soft-spoken and genuinely listened when I explained how to cut my hair. He asked me what I did for a living and we chatted about my job, then he explained that he works six days a week as a barber, and six nights a week as a road worker

What a hard life, I thought. We discussed how much sleep he gets between jobs – only three hours at a time, twice a day, he said – and I really felt for the guy. He was doing it honest: he could make more money burgling houses, or he could be in a gang, but instead, he chooses to work two jobs to scrape by. He gained my respect.

We also discussed money troubles – I noted how difficult it can be to make ends meet as a freelancer, he said the same about working two casual jobs with no holiday pay and no benefits. Then we chatted about his family – he had a wife and daughter he didn't get to see often – and he finished up my haircut (doing an excellent job, mind you).

I went up to pay and the haircut only cost $16. I normally pay "city" prices; $30 minimum. I thought to myself, "this barber has just cut my hair for 20 minutes and only brought in $16 for his boss. There's no way he's making any more than minimum wage." I looked at my wallet and there was a $5 note in there, so I handed it to him as a tip and said, "Here, man, you need this more than I do".

That was it. He never asked me for a single dollar. There was no obvious ploy, no requests, nothing. I left feeling like I made an honest man smile for a minute and to me, that was worth it.

For the subsequent hours, I thought continuously about this encounter. I really felt bad for this guy. My mood was polar and confusing: I felt sorry for somebody I'd just met, extremely fortunate for what I have, silly for the times I personally worry about money... all at the same time. I'm not living hand-to-mouth like he clearly is. I even considered making him my regular barber and giving him bigger tips next time – I can spare $10 here and there when a very good haircut is only costing me $16.

That evening, I relayed my experience to my friends. Before getting halfway into my story, one of them stopped me and asked about the barber's physical appearance, which I then described. "Yeah, he's a scammer, that whole schtick is fake", I was informed.

Apparently, this dude works as a casual at barbershops all over the city and has scammed colleagues and clients out of up to $1000 in "loans" they never see again. His trick is long-term relationship building with face-to-face contact and authentic vulnerability. I was then informed that the man actually has a gambling problem and conning people is how he feeds it – not a dollar is going to support his wife and kid.

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I felt right stupid for the next few days. This is how smart con-artists are these days. We're all so attuned to obvious scams that work through the web that we might get completely caught out by our human empathy when presented with real life scammers.

Needless to say, I've told my neighbourhood about this man so we probably won't see him around again. Do I regret giving him that $5? No. Yes, I got scammed, but the price I paid was insignificant. I feel a little older, a little wiser, and despite the fact he used that money for an addiction, his life IS clearly so sad that he really did need a fiver more than I did.