Lending money to friends and family

There is a particular kind of awkwardness that comes with lending money to a friend or family member. You give them the money because they need it, agree on when they'll return it, and then the deadline passes. Suddenly, asking for your own money back feels like an uncomfortable conversation you don't even know how to start. Someone shared a story online that captured this perfectly. They had lent a friend some money, and when the agreed repayment date came, they reached out to ask for it back. The response was: “What do you need it for?”