Serge Krouglikoff

You can save your friendship and your wallet.

July 26, 2017

If you eat out with other people a lot, you may very well have that friend—someone seemingly forever short on cash, or who simply never offers to pay in the first place. You're frustrated. (Your bank account is too.) What can you do?

"You probably don't mind occasionally picking up the tab, taking turns, or helping a friend out who is short on cash," commiserates Diane Gottsman, the author of Modern Etiquette for a Better Life and founder of The Protocol School of Texas. "But when the bill falls solely in your lap every time you go out, it's a different story." Luckily, however, this particular story can have a happy ending if you're willing to try out these expert-approved tips that will keep your friendship and wallet intact.

1. Employ a little humor.

Gottsman says it's A-OK to issue a warning to your cash-poor friend before you head out to eat, as long as you do so in a light-hearted way. She suggests saying something like, "I'd like to try out that new restaurant that just opened downtown. Do you want to try it? [If so] we better save a few of our lunch dollars, because I hear it's a little pricey but worth it." This way, your friend has been put on notice—and he or she really has no excuse to show up without the money to pay for the meal.

2. Don't initiate the invitation.

Here's a long-lost norm of proper etiquette: if you extend an invitation to eat out, you technically become the host of that meal—that can lead to the expectation that you'll pick up the bill. So, Sharon Schweitzer, founder of Protocol & Etiquette Worldwide, suggests you avoid issuing the invitation to eat out yourself whenever possible. And when your friend extends an invitation, "thank them for the invitation and ask if they plan to underwrite this meal because you have paid the last few times," Schweitzer says.

3. Set up new expectations.

The next time you and your friend make plans to enjoy a meal out, bring up the tab long before the server brings it to your table. Accept an invitation by suggesting you go Dutch, says Gottsman, or propose you take turns picking up the tab from now on. You can say, "Let's take turns picking a new restaurant and paying the bill," says Gottsman. And course, there's always the straightforward, honest route. Say to your friend, "I always enjoy your company but it gets pricey when we go out," Gottsman suggests. Then politely add, "Let's agree to pay for our own meals from now on."

4. Get the server on your side.

When it comes to a friend who's never offered to pay, one way to ensure you always get saddled with the bill is to receive a single check for both your meals. So, once you have snagged your seats, "quietly and immediately excuse yourself from the table, and discreetly find the server," advises Schweitzer, and ask the him or her to deliver separate checks when it's time for the bill.

5. Offer up an alternative.

If you don't want to chance an uncomfortable situation in a public place, Gottsman suggests you bring the meal—or the party—home, where you both can contribute something to the evening. Say, "I understand you are a bit strapped right now. Why don't we eat in and watch a movie. I'll bring the pizza and you provide the drinks," she says. Even if your friend can't bring much, he or she can almost certainly bring something.

Of course, making any of these changes could lead to an uncomfortable moment or two. After all, you're changing the status quo for a friend who's come to count on you to pay for his or her drinks and meals. But, "the real concern here is that your friendship is already being affected by feeling uncomfortable each time you are stuck with the bill," Gottsman encourages you to remember. So, while you run the risk of hurting your friend's feelings by being honest, "a real friend will understand and appreciate your candor. It shows you trust and value the relationship," she says.