About ten years ago, I gave a friend a credit card in his name for which I was responsible.
After a few months, I became uncomfortable with how long it was taking him to pay me back and I canceled his card.
He got angry and refused to pay me back for about $500 he billed on the card.
Over the past decade, I’ve tried three times to discuss this matter with him to no avail.
In response, I’ve let the friendship wither. We still chitchat on the phone about once a month — he’s been in poor health for about a decade — but I don’t go out of my way to see him or to help him because of his failure to this matter.
I’d say three times is my limit for reminding a friend he owes me money. After that, I write off the friendship (but not explicitly so, I believe in keeping cordial relations with as many people as possible, even people I don’t like or trust or respect).
(This blog post is not directed at anyone currently in my life with whom I’m doing business. Your accounts are all good with me. I was inspired to write this blog post by a friendly phone message from my former best friend who’s owed me $500 for a decade.)