I think the secret to success in lending to family and friends is to not really expect to see the money again (and still be OK doing it). This still doesn't so

I think the secret to success in lending to family and friends is to not really expect to see the money again (and still be OK doing it). This still doesn't solve all the kinds of drama and conflict that can come up (e.g. siblings can get annoyed with each other when 1 pays back a family loan and the other doesn't), but it helps a bit. I limit lending amounts to what I can sensibly afford, and I still have to apply judgement. I also gently knock back requests for "more" loans where there's been a large amount unpaid in the past.