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It's one of the toughest positions you could ever be in. Having a family member who you care about ask for money. There is never a good scenario that comes from this. It has lose-lose written all over it.
If you don't loan him the money, he will be mad. Whether you have great reasons or not, he'll probably be pissed.
If you do loan it to him, it can cause more trouble. I've realized that loaning money to family is like giving it to them. It seems that a statement like "I'll pay you back when business picks up" means probably never. People are much more lax with paying back family.
My suggestion is to only loan it if you have the money and won't need it. There is a good chance you'll never get it back.
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