How to Handle Awkward Money Situations

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

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The arrival of the bill at the end of a meal can be very awkward. What should you do when your dining companion insists on treating you, but you don't really feel comfortable with that? What about when you ordered a cheap meal and no alcohol, and your martini-downing friend wants to split the bill evenly?

[In Pictures: Celebrities with the Biggest Money Problems.]

There are three rules for dealing with a money-and-relationship problem: Nip it in the bud. Learn to say no. And don't lose sight of who the good guy is—you, not your friend or relative who's trying to make you feel petty for caring about money.

All three apply in these dining dilemmas. In particular, if you don't want a friend to treat you, say "No." Or make that "No, thank you. It's nice of you to offer, but I insist on paying for my own meal." If he or she refuses to take no for an answer, the next time you go out to dinner together, take the waiter aside at the beginning of the evening and tell him you want the check delivered to you. Then insist on paying it. If you like, you can tell your friend as you do so, "This time it's my turn. But in the future, why don't we just split the check?"

Why is this important? Of course, it's fine to allow someone the pleasure of buying you a meal. But if you allow that person to treat you to every meal, you are assigning to your friend the higher status that comes with being your patron. That's a dynamic best nipped in the bud.

As for the opposite type of problem—that is, the friend who wants you to pay for half of his martinis and chateaubriand while he pays for half of your iced tea and pasta primavera—the solution once again is to speak up. You won't be the first person to reach for the dinner tab and say, "It looks to me like your share is about $80 and mine is about $40." Nor will you be the first person to request separate checks or, if he does all the drinking, a bar tab separate from the food tab.

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