Does this scenario sound familiar… you’re on a limited budget (or on a diet) and you’ve gone out to dinner with friends. You order a salad and water. They order a cocktail, an appetizer, a main entrée, wine, dessert and another glass of wine. The bill comes and they say, “Let’s make this easy and split the check equally.”

Another situation that’s uncomfortable is when you’re out on a date and you don’t know who should pay. Is it always the man, the one who asked the other person out, or the one who makes the most money?

There are many reasons why it can be awkward when the check comes and you’re not sure who should pay. Below are some tips to help based on the most typically situations.

With Friends

  • Communicate early. If you’re on a limited budget, or you’ve had a bad experience in the past where you’ve ended up overpaying with this particular group, tell your friends ahead of time via text or before you order that you’re going to get a separate check. Say something like, “I’m on a budget right now so I’m going to get a separate check.” Chances are your friends will ask for their own check as well and will appreciate you speaking up.
  • Bring cash. If you think you’ll get too much hassle by asking for your own check, or if the restaurant won’t do that, then the smartest thing you can do is to bring cash in small bills so that you can just pay for what you ordered and then let everyone else put in their cards to split the difference. For example, “I’ve calculated my meal plus tip and here is my $27.”

Dining for Business

  • Dining with your boss. If your boss asks you out for a meal you can almost assume that he/she will be paying for the meal and writing it off as a business expense. However, it is always the right thing to do to offer to chip in. So when the check comes just be chill and wait for your boss to reach for it, but then you can do the “reach” and go to look in your purse or wallet and say something like, “Can I help with that?”
  • Dining with clients. If you are taking clients out for a meal you are expected to pay. However, if the person is a prospective client, then he/she may not want you to pay for their meal because they might feel obligated to buy your product or service. Always be prepared to pay, but if the person says they want to pay their share then go ahead and split the check.
  • Dining with co-workers. If you often dine out with people you work with, you may establish an alternating plan of who picks up the check. However, sometimes this gets awkward so you may want to set up the guidelines ahead of time. If you specially ask another person out for lunch then be prepared to pay, but if they say they want to chip in then you can say something like, “You can pick up the check next time.” Communication is key and either tell those you’re dining with or the waiter when he/she takes your order that you’d like a separate check. You don’t have to tell the group why.

On a Date

Okay, this is where it can get tricky. Whether it’s a first date with someone you know, a Tinder date with someone you just met, or you’re on your sixth date but you’re thinking of breaking up with the guy, there can be an awkward moment when the check comes.

  • Realize that times have changed. It used to be that when a man and a woman went out to eat that the man would pay. So much has changed since this “rule” was established and now:
    • There is more equality between the sexes and often it’s just expected that each person, regardless of their gender, will offer to pay for their own meal or for the other person’s meal.
    • Many women make more money than their male companion.
    • Some women don’t want to feel obligated to their male date if he pays for the meal if he’s expecting to be “paid back” in some other way.
    • Some men think they shouldn’t have to pay just because they are a man.
    • Many people are going on blind dates now from using dating apps and so there is more of an expectation that the couple will split the check.
  • Realize that old-fashioned manners are nice too. Even though times have changed, there are many people (many women) who still appreciate the gesture of their date offering to pick up the check. So, for the men who are reading this, I’ll tell you that your offer to pay for dinner will be appreciated. Another “rule” that you can keep in mind (and that some people still follow) is that the person who asks the other person out is the one who is expected to pay.
  • Be prepared to pay. Regardless of your gender, be prepared to pay for at least your share of the bill because you never know what the situation might be. For example, if you’re on a date and you don’t like the person you definitely want to pay for your own meal. You can say something like, “I’ve really enjoyed dinner and I’d like to pay for my own meal.”
  • Don’t argue. It can get out of hand when people literally fight for who “gets to” pay the check. Offer to pay, offer to split, but if the other person really wants to pay then you can graciously say, “thank you so much. I will pick up the check next time.”
  • Alternate paying. You can set up with your date that you alternate paying for meals. This way there is no “fighting” at the end of the meal and each person is contributing.

If you have etiquette questions or are interested in having an etiquette workshop delivered to your office, group, or for your children, please check out my website at FinesseWorldwide.com.