It starts with a simple gesture and good intentions. A family member in need (both distant and far), a friend down on their luck, a colleague facing temporary financial strain, etc. Lending money to those close often seems like the right thing to do, after all, it’s a way to be there for someone when they need it most. But what to do when the repayment stalls, or worse never happens as excuses multiply, or the relationship sours. What began as an act of kindness on your part can turn into a long-term ordeal of bitterness and regret.