I Warned My Son About Money. Then I Counted My Own Mistakes.

My son is 17, and he lent his friend $500.

Not all at once. Twenty here, fifty there, the way a tap drips. He told me this quite calmly. The friend will pay him back.

I asked how. The friend is also 17. No job and not close to getting one. There is no mechanism in the world by which this money comes home.

So I told him straight up: You’re not getting it back.

He nodded. He understood me completely.

He remains optimistic.

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I was 33 the first time.

A friend needed $2,700 to clear a credit card bill. He was an army regular, which in my head meant safe and stable, and I’m going to get my money back.

What I didn’t know was that he was doing the rounds. I wasn’t a friend he came to. I was a stop on a route.

Eventually the loan sharks got tired of waiting and turned up at his camp. You can imagine how that goes for a regular. He isn’t one anymore.

Here’s the part I don’t enjoy. He lives in my estate now. Some mornings I see him at the pool with a young kid (which I reckon is his), and I look at my phone with tremendous urgency, as though the void has just messaged me.

He does the same thing. We have an arrangement. Neither of us agreed to it out loud.

So the $2,700 is still charging me but not in money. Every time I make myself invisible in my own estate, that’s the interest.

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Then the ICO. Twenty thousand Singapore dollars.

This was the first crypto peak, when everybody knew a guy. My guy was someone on a roll in crypto, and he explained it to me in the tone people use when they’re being generous with you.

Then he beat his chest. If anything happens, he said, he’d cover it himself.

Nobody asked him to say that. He offered it. And I heard it as reassurance instead of what it was, which is a man promising to pay a bill he could not pay.

I won’t pretend he took advantage of me. I wanted the $20,000 to become $60,000 while I slept. He was just the permission slip.

Nothing happened. Nothing was ever going to happen. And he never compensated anybody, because of course he didn’t.

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The last one is the worst, because I saw it coming.

After my mum passed, I wrote about it. A LinkedIn connection reached out with his condolences. We met in person, and he told me his mother had passed too.

Four years before mine, he said.

Four years is long enough that he was out of the worst of it. Short enough that he’d still remember what the worst of it felt like.

Yup, this guy gets it.

In subsequent meetings, he mentioned he does a bit of day trading on the side. Doing well. Would I like to come in?

I declined politely, but he asked again and again.

Before I gave him anything, I went and read his profile properly. Something in it didn’t sit right. I couldn’t tell you what. Nothing you could point at. Just a low hum, like a room that’s slightly too warm.

I sent him USD $1,000.

I want to be precise, because “I got fooled” would be a relief. Fooled is fixable. Fooled means next time I read more carefully.

But I did read carefully. The hum was there. I paid the money to stop hearing it.

Because the alternative was to sit across from a man whose mother had died and say: mate, I’ve looked you up, and I don’t like what I see. That sentence costs more than a thousand US dollars. So I bought my way out of saying it.

Updates came for a while. Then they stopped.

I checked his number recently, and he is not on WhatsApp anymore.

He’s still on LinkedIn though. So I know exactly where he is. And every so often I go and look at the profile again, scanning it, hunting for the thing that would prove I couldn’t have known.

I never find it. What I’m actually checking, if I’m honest, is whether his mother existed.

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So I don’t lend now. Not to friends, not to friends of friends, not even to someone crawling towards me, leaving a blood trail on my floor. If I ever hand over money again, it goes out as a gift, and I will never ask about it, and I will not be waiting.

That’s what three of these buys you. It’s expensive tuition, but it took.

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My son is out $500 and still thinks his friend will come good.

I’m out a lot more than that, and I still open a stranger’s profile wondering if his mother was real.

He nodded when I told him. He understood me completely.