Speaking from experience, only provide the cash if you're ready and willing to lose it with no hard feelings. That last part can be harder than it sounds. We've done it before, with mixed results. The last time I did it (last year), my friend had been out of work and needed to move. We gave him $200 or so, and so he wouldn't stress out about it, we just said to pay us back if/when he could. We had lent him money before, and it had been paid back very slowly. The guy was screwed, though, and is a good friend. I told my wife we'd never see the money, and we both agreed it was the right thing to do. I still think it was, but when the tax return came in and he bought a big screen TV with no mention of the $, it kinda rubbed me the wrong way. I got over it, though, because from the beginning I was more or less considering it a gift.