If you're never getting that money back, you might as well forgive them and forget it. Then at least you'd keep the friends.
It seemed obvious that it was a small gamble for me, a big gamble for my friend, but he was doing all the right things.
VCs don’t waste time with concerns over failed investments.
When you hand over some money, you are accepting the risk.
Including complications, which are likely. Treat the money like a gamble, not the friendship.
I was really glad I did. My friend created a successful business after working toward that with major ups & downs for over ten years.
Then he got cancer, and died a year later. I got no money back. But it was the best investment I ever made. His dream came true and that mattered so much to him. That he pulled it off, and his customers loved him and his business.
Don’t invest in a friend if the investment isn’t about genuinely helping them.
If you can afford to.
This is common advice because it turns good relationships bad, that manifests as viewing former friends as shysters
I've personally lent money to friends when they needed it, and been paid back once they got stuff sorted out.
Though in my younger days I was far less careful, so lending money did indeed go poorly.
Even in the case you describe, it’s much better to gift it: “if you want or are able to pay me back some day, go for it, but I don’t expect or need it.”