Could it be that by loaning more money than they expected, they spent that money and then entered into a negative cycle where they were never able to gather the

Could it be that by loaning more money than they expected, they spent that money and then entered into a negative cycle where they were never able to gather the money again? I used to do the same thing as you on a smaller scale (in the hundreds, never the thousands). I noticed that while loaning more money made more sense to me, whenever I did that it was a struggle to get the money back. Meanwhile when I loaned the exact amount, it more often came back. I lost several friendships this way for a short while, with the only way to get the person out of the guilt cycle to surprise them at some random Christmas or birthday with "my gift to you this year is to give you the money you owe me". With them later telling me that they were feeling so guilty about the money they avoided talking to me because every conversation would make them feel miserable. Now when I loan money, I enter the amount in an app we have in common and then actually put in place a (vague) payment plan. I find it helps people structure the entire situation and since they get to pay some money back the guilt is less present. It seem to remove the expectation that they need to gather the full amount before paying back.