If you dished out the invites, you should technically pay, an etiquette expert told Moneyish
“The Rules” is a Moneyish series where we define the rules around sticky money or workplace topics like giving an allowance, who pays on a date, combining finances with your partner, and more.
Settling the bill can be awkward, especially when you’re out on a first date, with friends or even distant family. Apps like Foodivide and Splitwise can help do the math on splitting the check if you want to pay the precise amount of what you owe at the table.
But forget never having cash — half of respondents to a 2017 U.S. Bank survey of more than 2,000 participants said they carry cash less than half the time while they’re out. Who is actually supposed to pay after you’ve swiped right or are out to dinner with family?
“Sometimes it gets hairy when people look at the bill and say, ‘You had the $10 salad; I had the $14 sandwich,’” etiquette expert Karen Thomas told Moneyish. “It’s sometimes easier to have one person pay, and transfer them the cash.”
Still, figuring out the politics of who pays can be tricky in the moment. Here’s how to navigate the dreaded bill in any scenario.
Dinner with family:
When you’re going out with family, whoever does the inviting typically foots the bill. So if Dad, Mom, an aunt, uncle or cousin does the asking, expect them to pay — but it’s always worth offering to kick in a few bucks, especially if you can afford to, etiquette experts note.
“Usually once you’re out on your own, you should expect to pay the bill, even when you’re out with family,” Thomas said. “As the parent, I usually pay for everything when I go out, but now that my son is older, sometimes he’ll invite us and he’ll pick up the tab.”
If you’re out with siblings, don’t expect the person who makes the most to foot the bill every time. It’s okay to let a sis or bro pick up the check now and then, Thomas said, but be prepared to reciprocate the gesture, or simply split the tab each time to avoid an argument.
“Discuss ahead of time rather than getting there and not saying anything, and assuming she or he is going to get the bill or visa versa,” Thomas suggested. “Go into it with the expectation that you’ll split it. It should never be assumed that just because the last time you went to lunch and she or he paid that they’re going to pick up the tab.”
Meals with friends:
Always expect to go Dutch when grabbing drinks or dinner with friends, Thomas said.
“It’s usually implied that if you’re with friends, each person will pay their own way,” she said. “If there’s any reason why you can’t pay for yourself, don’t go, or discuss with a friend beforehand and say, ‘I’m short this week, do you mind picking up the tab and I’ll get you back next time?’”
It’s always easiest to split the bill among everyone who joins instead of splitting hairs over the cost of separate menu items, especially if it’s a big group, Thomas added. Another way to avoid the hassle is to have one person foot the bill, and use Venmo to pay back the friend exactly what you owe — that way if you get something small, you don’t get stuck paying more than you should.
“Let’s say I grab the check, knowing full well you’ll Venmo me the funds — that’s absolutely fine,” Thomas said.
Whoever does the asking should presumably be the one to pay the bill on a first date, Thomas insists. But if you feel strongly about going Dutch, that’s perfectly fine too.
“Let’s say I call you up and say, ‘Would you like to have dinner with me?’ Then it’s implied that I will pay,” said Thomas. “I invited you. Whomever invites pays.”
For those on dating apps like Tinder and Bumble, Thomas still says whoever suggests the date should technically pay, but if you want to avoid the awkward conversation when the bill comes, simply say beforehand: “Let’s just split it and make things easy.”
Working lunch with your boss:
If your boss is asking you to a lunch meeting to talk about work, expect that he or she is going to pick up the tab. “If work is actually being done, the implication is that the boss will pay. In most cases, there is an expense account. If you’re unsure, you can always offer when the bill comes,” Thomas said.
On the reverse end, if you’re asking to meet with your boss outside of work hours to get career advice, then you should be the one to treat, Thomas said.
“It’s not considered brown-nosing,” she added. “You’re conducting the business; you have questions, so you pick up the tab.”
If your boss insists on paying the bill, however, it’s fine to stand down. The offer shows that you appreciate his or her time.
Cocktails with colleagues:
Treat grabbing a drink with your colleagues like you would going out with friends — split the bill, Thomas said. “Everyone should be responsible for their own tab,” she said. “If you want to buy someone a drink, you can say, ‘Put it on my tab.’”
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