I've always felt that my job is to help people and not to intrude. So when someone tells me she is having a financial crisis, I used to take her word for it, because I felt it was inappropriate to ask questions about finances. While financial matters are generally considered private, is it appropriate to ask questions (and to what extent is it apporpirate) if someone is begging for your help? And what kind of questions should I be asking? I thought about pointing to people in her life, like "Can so-and-so help you?" But her typical reply is "They are not helpful" (regarding other things). So do I need to get more specific?

I've troubled myself and troubled other people to help someone and later found out she is going on vacations, and she was withholding information about additional income sources. I am not made of money, so this is a big risk for me.