7. A & B
A friend’s family fell on hard times. I had an emergency fund and let them borrow a five-digit amount of money to swing their mortgage and groceries.
A few years go by and there’s no attempt at paying me back, the couple gets divorced and life goes on.
One day the dude emails me and shows me an ad for a classic car for $11000 and asks me what I think (he knows I’m into cars).
I give him my opinion but add at the bottom that maybe he might consider paying me back before spending money on frivolous toys (he already had two cars).
He went off on an angry two-page rant about how his ex-wife was the one who f*cked me over and he was ripped off much worse, blah blah blah and then never talked to me again.
It was an expensive lesson to learn from A, never loan out money you can’t afford to lose and B, if it’s friends and family, give them the money, don’t loan it. It’s not worth risking friendships over.
I’m still owed that money and it’s been 15 years.