Real Simple etiquette expert, Catherine Newman on how to ask a friend to repay a loan.

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Q. In 2009 my friend’s husband asked for a divorce. My friend had little money of her own and couldn’t afford a lawyer, so my husband and I offered to lend her $1,500 to help her retain an attorney. She was grateful and promised to pay us back in small increments. I told her to take her time—but in four years she hasn’t handed over a dime, even though she has remarried and is financially secure again. How can I ask her to repay the debt without upsetting her?

J. O.

A. You’re a great friend. The good news here is that your generosity helped someone in a stressful situation to find peace, for which she is doubtlessly grateful.

The bad news? She has put the past so far behind her that your favor may be lumped in with other events from a tough time that she would rather forget. Since a significant sum of money is at stake, you will need to remind her.

Luckily your friend’s present happiness can help smooth out this potentially thorny interaction: “My husband and I are so thrilled that you’ve moved on to a better relationship,” you can say to her. “And I’m sorry to bring up a difficult time in your life, but I’ve been wanting to check in about that money you borrowed.” Most people would be mortified about letting such a hefty sum go unreimbursed. Chances are, your friend will feel the same way. Regardless, you’ll get the conversation started so that she can repay you—and both of you can leave behind the last dregs of her bad marriage.

Catherine Newman

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