Ugh... This touched a nerve. Surely, if you have a semi-unlimited amount of money (way-way more than will ever be asked from you), it's easy just to loan and fo

Ugh... This touched a nerve. Surely, if you have a semi-unlimited amount of money (way-way more than will ever be asked from you), it's easy just to loan and forget. I think it's a much harder game for the rest of us. Also, it has a built-in assumption that people will self-limit what they are asking. I learned the unpleasant way that people don't. At some point in my life, I had a friend who was constantly asking for smallish amounts and conveniently forgetting to return them. Each ask for definitely in the category that I didn't care whether it was returned or not, but if you accumulate all of them, it was an amount big enough to care. After numerous unpleasant interactions with the money subject, I just decided to stop this practice. That being said, I feel like it's critical to not become too thick-skinned. Sometimes people do need help and they are truly in a bad place and dismissing their ask just based on some other problematic person is not good.