Question: I am not independently wealthy, but I have enough to be comfortable. My brother has always struggled with money. Recently, he asked me to lend him money to help buy a car. What should I tell him?
Answer: In my experience, loans to family and friends tend to complicate relationships and often lead to misunderstandings. This may sound harsh, but if you lend money to a friend, you had better be prepared to lose a friend. And if you lend money to family, chances are you are setting yourself up for some unpleasant drama.