Lending money to "friends" and acquaintances: What are your horror stories?

I honestly can’t wrap my head around how gullible and just plain naive my sister-in-law is...

Look, I learned my lesson way back when—I lent money to a "buddy" once, and I am never, ever doing that again.
I was 19 at the time and I handed this guy $200—which, let me tell you, felt like a small fortune back then since I’d been saving up—and he looked me straight in the eye and promised to pay me back in two weeks.
And I actually believed him. Just took him at his word.
It ended up taking me an entire year of constant headache and chasing him down just to get my own cash back.

So, fast forward to now: my sister-in-law goes out and takes out a personal loan$10 from the bank to renovate her place.
Keep in mind, this is our apartment (mine and my wife's) that she lives in.
We were starting to think it was super weird that she was falling behind on her rent payments to us.

Then comes the absolute bombshell!
She tells us she can't pay because she lent the money to her "acquaintances" and "friends"...

In other words, she basically handed it over to scammers.

My wife and I were just sitting there in total shock.

I mean, does she really have to get burned this hard just to realize that people don't just hand you money for nothing?

Man...

It's awful.
The worst part? She actually feels like she owes *them* a favor, all because they sold her some shady crypto or whatever.

If I borrow anything from people who have been good to me, I make it my absolute priority to pay them back as soon as I possibly can. It’s just how I operate. And look, if I lend someone money, I fully expect to see those funds returned eventually. Now, I’m not being unreasonable—I don't expect an immediate payoff if the person is currently going through a tight spot or doesn't have the cash on hand right this second—but once they are back on their feet, I definitely expect that money to come back to me. 🙂

So, I ended up lending some cash to a buddy I've known for about ten years now. There was this one Saturday night we were heading out, and the guy realized he’d totally forgotten his debit card at home. I just covered him $100 and he paid me back the very next day. Honestly, I only lend money to people I truly trust—like my inner circle—not just some random acquaintance I see passing by. Personally, I’ve never really been the type to lend money to anyone, and I’m pretty hoping I never actually have to go down that road.

I honestly don't know what life has in store for me... but right now, my only thought is that I'll need to be in good health (God forbid) just so I can actually approach someone to ask for a loan.
My first move would always be to turn to my mother... and then everyone else after that.
As far as lending money goes, I’ve had some incredibly bad experiences, even when it involves close friends.
The money is never returned on time. Or worse, it comes back in twenty tiny installments. That isn't really a repayment; it's just an inconvenience.

I once lent a close friend a massive amount of cash, and let’s just say I never saw a dime of it again. After months of awkward tension, we eventually settled on the fact that constantly badgering him for my money was just too uncomfortable 🙄

Don't get me wrong, I'm talking about real money here. Small loans of 100-$67 to cover a night out don't count; I know those will show up in my Venmo by tomorrow morning.

Just five bucks for a snack, he gives me five bucks for a snack, and that's how it goes. 😬

There's no way I'm lending anyone more than ten dollars, unless it's my parents or my sister.

I suppose I don't see much of an issue with lending someone $100 or so $67, especially since I don't typically ask my friends to pay me back when they’re always there to lend me a hand whenever I'm short
.
The real headache arises, I think, when you find yourself lending someone a larger sum, say $1,000, and then suddenly you're the one in a pinch, but they won't return it despite clearly having the funds. It almost feels as though you have to beg for your own money... it's happened to me personally, and I imagine it's a situation many others have faced as well
.

People say:

If you want to cut someone out of your life for good—just lend them some money. 😬