The lesson for me: if you loan to people you are close to, and you expect to be repaid, you will end up in the undesirable position of judging everything they spend money on in relation to the debt they owe you. Not fun. Unless you can emotionally write the check as a gift without any strings (and financially as well, of course), don't do it. People will almost always have a different view of the priority of the obligation (usually unsecured) than you might.
+10.
My wife once loaned a few thousand dollars to her brother for him to pay his kid's college tuition. I did not know what the term was, and since it involved her brother I stayed out of it. He finally repaid it without interest a few years later, once his child graduated and had a job.
During that time, visiting him, I saw new TVs, HiFi, PCs, cars being bought. Perhaps my wife's term was "At graduation", or "Whenever you feel like it", and so my BIL took it literally.
I kept my thinking to myself, and did not raise any question. The funny thing is that we had given him money previously (also a few thousand), when he was not doing as well and there was no prospect of him ever paying back. My wife made the latest a loan only because his financial situation was improving. But it also raised my expectations, and caused me to doubt his character. I had to say that he was a good man in all other aspects.
But if I were him, I would repay my debt ASAP. We have borrowed from a friend once in my life when we were just starting out, as described in another thread. We made every attempt to pay that back ASAP before we even thought of buying anything.
We still give money to relatives from time to time, but will never make loans again. And of course, it is great to be in the position that we do not have to ask family and friends for money.