We’ve all experienced it: That uncomfortable moment during a night out when the bill arrives. Am I picking this one up? We silently weigh our options, factoring in the people present (friends, colleagues, a date), the age of the guests, the professional expectations, and yes, sometimes even the genders involved.

You have to decide in that split second whether to reach for your wallet, and it’s not always so clear what you’re supposed to do. So here are some etiquette tips that will help you be prepared, before you face the bill.

1. Out With a Client

At work, the client comes first—and if you’re meeting her for drinks or a meal, you should treat her accordingly. It's customary for you to cover the cost, and any other expenses (coat check, taxi fare) as well. Consider footing the bill as a future investment in a good business relationship.


2. Out With Your Boss

If you’re out with your boss, either during the workday or after hours, she’ll often offer to pay—and there’s no need to argue with that. But, particularly if it’s your boss and your team and there are group logistics to handle, this can also be an opportunity to take charge and show that you’re confidently in control. Let your boss relax while you take care of the details like hailing a cab, tipping the coat check, and being the one to put the meal on your company credit card (so she doesn’t have to deal with getting reimbursed).

You can tactfully let your boss know in advance that you’re happy to take care of all the details. She’ll be impressed, everyone present will be grateful, and there will be no potentially awkward moments when the check arrives.

3. Out with Your Co-Workers

Dining with co-workers can be tricky. At lunch, it’s generally assumed that everyone will get separate checks, but the game changes at dinner. In general, be prepared to split the bill down the middle—it’s not worth quibbling that your entrée was $2 less than everyone else’s. But, if you anticipate that the group will order multiple bottles of wine and you only drink water, don’t be afraid to speak up at the beginning of the meal and ask for a separate check.

4. On a Date

These days, general dating protocol says that the asking party should assume that he or she will pay—though society still often dictates that guys should pay for at least the first date, regardless of who asked whom. In any case, when dating, paying the bill is a sign of generosity and interest in the other person. So if your date offers to pay for dinner, you can graciously accept for the first couple dates—but after that, it’s time to reciprocate the offer.

5. Out with Your Family

In family situations, don't automatically assume that your parents will pick up the meal, even if they try. It’s common courtesy for employed, adult children to offer to pay the check at a family dinner. Expect that your parents may argue—and if you are determined to treat them, arrive in advance and give the server your credit card and request the bill come directly to you at the end of the meal.

While there are plenty of other potentially awkward payment situations, deciding who pays boils down to professionalism and social consideration. Be generous, be savvy, and when someone else insists on treating you—just be gracious.

Photo courtesy of Stephanie Wesolowski.