Lending money to someone you love can feel like the natural response when a family member, partner, or close friend is struggling. Yet a financial favor can quickly become a source of resentment when expectations are unclear or repayment does not happen as planned. Bankrate’s 2025 Financial Taboos Survey found that 70% of U.S. adults had lent money or covered a group expense expecting repayment, and 55% of those people reported at least one negative consequence. Before lending money to someone you love, consider these seven checks that can protect both your finances and your relationship.