Should he help?

[Bahasa Indonesia]
My friends (let’s say a male, “he”) is quite well off. An advantage that leads to dilema. An advantage that are often misused, abused, by other people.

People then think of him as a source of unending wealth. There are always ‘friends’, family, relatives who come to him to borrow or ask for money. With various reasons/excuses. Illness. School tuition for the children. Pay the rent. Payment for other debts (with interests). Opening a business.

When this happens, my friend is always confused, should he help? Not that he is a scrooge, he is just uncertain. How does he know that that person is honest and not playing around with him? What's with the excuses? Especially when it is not the first time that that person comes to him.

I understand the confusion. I too am unsure. Should he help?