This is weird because it just had some kind of conclusion.
I loaned one of my oldest friends a significant amount because he came and asked me for it. I was reluctant but he had been my best man, etc. We used to see each other pretty often and I had known him since 7th grade.
But he said he would absolutely pay me back within a few months. I said "first of all you have to promise me it won't affect our friendship." of course not he said.
I called him a few months later. "What are you doing?" I asked. "Oh, we're working on an extension on the house." Really?
A month later he breaks the news to us -he has cancer. But he is still playing in bands & stuff. We see him around.
Like you I didn't pressure him until about a year later, and then I called to ask how he was feeling, etc. Everything was under control, he said. So, I said "I think you need to start paying me back when you can, so he brought me a check for 20% of it. We and his wife went out to dinner, etc.
The next time I called him he said "You know what, you don't want to be my friend, I'm a real ass*. You don't want to know me." I knew where he was going with that, so I said "Hey, this is not how I feel... (you know)."
He and his wife continued to have parties, go out, have friends over, but we were off the friend list. Never a call. We even tried popping by a few times and they were just never home. This started in about 2008.
He just passed away from a sudden relapse of the cancer. He had been doing well. So, his wife invited us to the casual get together, barely acknowledged us.
About a week later she called me and said "You know, I have to say you deserve an apology." But I still don't if she ever knew about the loan. She didn't mention it, she just said "He had a real change in personality the last few years."
He was one of best friends, and the fact that he did that to me really bothers me. Was I supposed to be the one to say "you have cancer, forget the money?" he acted as if he was doing fine, plus the his wife has a closeknit family that I'm sure she is doing well financially. He either never told her about the loan or she decided that since he passed away it wasn't her responsibility.
Now I wonder if he knew he had the cancer when he borrowed the money. That's sick of me, I know, but the timing was very close and I can't help wondering.
The thing is - it isn't just the money or just the friendship, its mostly the friendship, but its really both. If he had come to me and said "I'm sick, I can't pay you back, but I hope we'll stay friends" that would be one thing, but he wrote me off but had a very active life with other friends - because of hid debt. Very rude of him. So, am I supposed to take the high road and say "well, the guy was sick, I understand?" I can forgive him, but I just can't ever say "I would have done the same thing if I was in his shoes."