We are talking about friends and relatives here. Lets us not become bankers in our spare time. Lest we find ourselves friendless and without family with our down luck. The control here is simple; you either have the money to help this loved one or you don’t. As embarrassing as it is to ask for help, it is equally as embarrassing not to be able to render it. You have no control over another persons concept of honor or fair play. You only have control over your own concepts and whether or not you are going to reflect these concepts within your life or not.
Personally pestering a loved one over a loan isn’t worth the drama to me. What I have purchased is the direct knowledge of their character and value system. I do not see being able to carry more than my share as weakness. Only the strong carry more than their share. If I had a relative who needed help and I did want the person pestering me I would perform a mitzvah and give the money anonymously and preclude and need to pay me back or setting myself up with false hopes of being paid back.
People who always have to have their share aren’t friends you want to have anyway. Generosity and philanthropy are the mark of a successful person. Beating the last buck they owe out of them is the hall mark of the mob. I have never respected bankers as a profession. I feel that they take people’s money and loan it to other people; then to protect the load they use insurance (that they sell) and skim off both while everyone else goes to work. Becoming like them isn’t a life goal of mine.
If your friends are shallow and vain, then you need to examine how you make friends. As for mine, if they got a bad deal and I had the money there wouldn’t be a problem. I have had friends that helped me and I treated them like brothers and sisters but that is why they are friends. If one of them was hurt badly and couldn’t repay me I would hope that I was bright enough to see that as I was giving them the money.
I’m not telling you to throw your money away on lost causes. But helping a friend and giving aid when it is needed is the mark of family and friends counting the pennies and demanding your pound of flesh is for heartless, thoughtless, blood sucking bankers.