While harder to say 'no' to a family member I think with them you need to scrutinize all the more closely. I have a brother in need regularly and he hints (usually) or comes right out and asks for help. But I know for a fact he makes a reasonable income. His problem then is his not budgeting and spending his money on non-essential items so that by the time it comes around to pay his bills he comes up short. The last thing I will do is give him money as I know it won't go towards the necessities. He would just blow it on something else he doesn't need. My solution? I have him and his family over on occasion for supper.

You really need to ask yourself 'why' does the person need money and what they are likely to spend it on. In the case of the friend I previously mentioned, I suspected a drug addiction was the root of the problem. Consider the friend/family member's lifestyle. What are they spending their money on? Is the problem then truly a problem of income or spending habits.