Question: Someone I’m friendly with asked to borrow money, and I feel comfortable just lending it to her. But I once heard that Jewish law requires witnesses. Is this true?
Answer: If it is an amount that, if the person would say that they already paid you, you would pardon it and not take them to a Din Torah (adjudication in a Rabbinic court according to Torah law), then you do not need any witnesses or other corroboration. However, if that is not the case, then you should have witnesses. By the way, an IOU note with the borrower’s signature is just as good.
Best wishes,
Rabbi Azriel Schreiber