Two-bit Guru | Giving money to friends | Photo of a Christmas card with a $100 bill sticking out of it.

Four months before Christmas one year, a friend complained that his small business wasn’t doing as well as he’d like. I commiserated, and once we’d opened up the topic of ain’t-times-tough, it became a regular theme. Since things were bad for him, I couldn’t very well say they were good for me, although they were.

He and his wife had always been there for me and I felt sorry that they weren’t doing well. I decided to send them a Christmas card with a hundred-dollar bill in it.

The holidays came and went and I never heard from him. A suspicion moved forward from the back of mind that the bill hadn’t gotten lost in the mail.

About a month after Christmas I phoned him. Yep, he said, he got the money. No thanks. No appreciation. For sure no gratitude. I realized that I had insulted him. I improvised a story that the money was for all the favors he’d done me in the past, and this was sort of a repayment. Yep, sure, he got it all right, but he didn’t buy it. His feelings were hurt.

I had learned my lesson—be very careful when giving money to friends–but, like grade school grammar, I hadn’t learned it completely.

Several years after that, a friend told me of a mutual acquaintance who needed some quick cash. I looked the guy up. I offered him a hundred dollar loan or more if he needed it. My terms were that I expected no interest and he could either pay me back whenever, or when he was able he could give the hundred to somebody else. He gratefully accepted my offer. When the movie “Pay it Forward” came out years later, I proudly acknowledged to myself that I had invented the concept independently.

I didn’t see this fellow for a long time, months if not a year. One day I bumped into him at the grocery. You’d have thought I was the devil incarnate, the way he backed away from me without a word. I guess he thought he owed me the money and was embarrassed that he hadn’t paid up. Apparently pay it forward wasn’t a viable concept for him. Or maybe he was ashamed that he’d needed help in the first place.

Unlike grade school grammar, this time I got the lesson in it’s entirety: Be very, very, very careful when it comes to giving money to friends and acquaintances.