How to Handle Awkward Money Situations

Etiquette experts offer tips for responding to needy relatives and other tough financial spots.

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If you've ever had a family member ask you for a loan or been asked to split the bill when all you got was a salad, then you are familiar with the awkwardness that can surround money and relationships. In Isn't It Their Turn to Pick Up the Check?, Jeanne Fleming and Leonard Schwarz offer strategies for dealing with the most cringe-inducing scenarios. U.S. News spoke with Fleming and Schwarz about how to handle relatives who ask for loans, splitting the check at the end of the meal, and when, if ever, to lie about money. Excerpts:

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Does lending money within families usually hurt or help relationships?

Forty-three percent of the people we surveyed told us that when it came to the largest amount of money they'd ever lent a friend or relative, they were never repaid in full. Moreover, 27 percent said they never got so much as a dime back. That's a lot of people being stiffed and, in turn, a lot of resentment being created. And what these statistics don't capture, of course, is the amount of effort many of the people who weren't stiffed had to put into getting repaid—a chore no one enjoys.

When a friend turns out to be less than honorable about a loan, at least you have the option of no longer socializing with him or her, if you choose. But when the people who stiff you are family, you may have to suffer through, say, a Thanksgiving dinner at which they brag about dining at a new upscale restaurant—a place you feel they had no business patronizing until their long-overdue debt to you had been repaid.

So, to answer your question: While there is often good reason to lend money to a relative and real satisfaction to be gained by helping out a loved one, the fact remains, you are entering a relationships minefield when you do so.

It seems as if a lot of questions people have revolve around a hesitancy to be honest because it might hurt someone's feelings. You often advocate for honesty, but when, if ever, is it best to fudge the truth?

You're absolutely right: We're all for honesty, for being direct. But more fundamentally, we're for sticking up for yourself—whether it's by asking for a loan to be repaid, by refusing to let your sister help herself to all of your mother's nicest things after the funeral, or by explaining to your neighbor that it is a problem that his new fence is two feet over the property line.

Not that there aren't occasions when there's good reason to let things go. Let's say, for example, your brother, with whom you are close, borrows your car and puts a large dent in the hood—a dent he is unconscionably slow in having repaired. If you can afford to pay for the repair yourself, you may be better off to do just that and stop being mad at your brother. That said, you should also stop lending him your car.

What's the most common awkward financial issue that couples face within relationships?

Conflicting expectations. Consider this: Some people believe you should never charge interest on a loan to a family member, while others see nothing wrong with doing so. Some people expect the parents to always pay when the family goes out to dinner, even when the children are working adults, while other people do not. And some folks believe the only fair way to divide up an estate is evenly among the children, while others think it's appropriate to consider how loving, supportive, and helpful each child has been.

Conflicting expectations such as these are common. And since courtship typically doesn't involve vetting your spouse-to-be on such issues, an otherwise happy marriage can run into real turbulence when, for example, the husband discovers that even his wife never expected her brother to repay the $1,000 the couple lent him.

Another trouble spot is secrets. It may be that the wife is slipping money to her family and not telling her husband. It may be that the husband is a spendthrift and the wife feels she needs to hide her bonuses from him. Or it may be that the husband is secretly investing in the stocks of companies that he knows his wife feels are not socially responsible. Whatever the secret, when it comes to light, the person who was kept in the dark feels betrayed, and a sense of betrayal is, need we say, never good for a marriage.