Should I Trust him after he Kills my heart?

You are 20 yrs older than him, but it's seem to me that you are more naive than him. It's so obvious that he is just after your money. Whether it's true or not that he is owing "Tailong" you should not borrow him any money. If you borrow him this time, he will keep borrowing from you until you are in great financial crisis again. By then, he will leave you.