"Fastest way to ruin a relationship is to lend money.
There really is no other answer.
I always give money if the person needs it and I have it. Otherwise…"
"Give them one chance to prove themselves worthy of a loan.
Make the loan for a much smaller amount than they ask for so that your losses are low.
If that doesn’t work out, just quote that as an example the next time they ask for money."
"I try hard not to ‘lend’ money, only give it without expecting it in return. That way it prevents me from giving more than I can manage and the relationship is not damaged. That said, no one has ever asked me for more than $100."
Would you ever loan your friend money? Have you?