I've learned to evaluate the situation with attention to the character and personality of the person asking. Some people would never want to impose on others, so if they're asking for money then you can guess the difficulties that drove them to this point. Others seem to be takers in many ways, and it becomes easy for them to ask for money.
I also try to recognize if helping with money helps with a problem, or only addresses an outcome. My extended family has a history of helping others out when they need it, but we have one family member who makes bad decisions and wastes their money. We love them and would do almost anything for them, but we won't give them money.
Doing the right thing sometimes means not choosing what initially appears to be caring and helping.
Always ask yourself what kind of a relationship you have with someone. Offer to help in ways not giving them money - that often shows their real intentions.
That said, if I'm going to make a mistake, I'd rather make the mistake trying to help out.
Not real clear, right? That's life. Try and do the best you can. :)
