Lending money to family, and why I have stopped. I have done it four times. Twice it came back, twice it did not, and the two that did not are the ones that changed things — not because of the money, which I could afford, but because every subsequent conversation had it sitting in the room. The advice everyone gives is "only lend what you can afford to give away", and I think that is right about the money and wrong about the relationship. What you cannot afford is the asymmetry. They know. You know they know. There is no amount small enough to be invisible once it has not come back. What I do now is give a smaller amount and say it is a gift, out loud, once. It has cost me less and I have not lost anyone over it. It also feels slightly dishonest, because I am managing the relationship rather than helping, and I have not worked out whether that matters.