Dear Prudence

Help! There’s a Certain Part of Dining Out That Stumps Me Every Time. I’m Not Sure There’s a “Right Way” to Do It.

Prudie chats with Lizzie O’Leary, host of What Next: TBD, about an etiquette conundrum that has caused a lot of heartburn.

A restaurant check between two speech bubbles.
Photo illustration by Slate. Photos by tovovan/iStock/Getty imaegs Plus and Seng kui Lim/Getty Images Plus.

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Dear Prudence,

When dining out with a group of friends, what’s the proper way of splitting the check?

— Down the Middle

Jenée Desmond-Harris: I’m sorry. No wedding drama, no juicy relationship issues. I just chose this one because I felt like talking about it. And I actually think it’s interesting. And it’s the subject of many social media debates in a way that annoys me.

Lizzie O’Leary: You are a sicko. I love it. I think we need to set some parameters here. Because there is not one answer! Important questions are: How many people are we talking about? Is there wild economic disparity involved? What about alcohol? and Are we all eating similarly priced things? Oh, and there is also a level of friend closeness that is very relevant. Like, if I am with my real besties, I am gonna be more honest about all of this. Recently, I was with two college roommates and we were splitting the check at a place that we could all afford, but I had booze and they did not. So I paid the tip. That kind of thing.

But I think a more vibes-based question is do you want to do a full accounting and Venmo situation (I have used the app SettleUp) or is this “Oh hey it’s fine let’s just split it three ways” even if it’s not totally equal. Hit me with your thoughts.

Jenée: Well, yeah. That (there’s not one answer) is exactly my thing. Which I guess isn’t as original as I thought. There isn’t a rule about this! It depends! And it bugs me when people act as if there’s a right way to handle this (or to handle who pays for dates, or whether you have to pick up your friends at the airport or expect them to get an Uber) because it’s informed by culture and the closeness of the relationships, but most of it really comes down to how much money everyone has and specifically whether the amount of money in question could derail their budget for the week or month.

So I’ll say that for me, a full-grown adult who is a professional and has friends who are professionals and generally isn’t eating out at wildly expensive places that serve an ice cream sundae with actual gold flakes for $500, splitting the bill evenly works and feels easy and fair. I just go into the experience knowing that there is a price to group meals that is going to involve someone’s insistence on ordering one thing of calamari for each end of the table and someone else proposing that we get the disgusting bread pudding to share. It’s like a cover charge for the company and the good times and it is not going to mean I can’t buy the toothpaste I need.

But if someone is barely making it every month, the thing that creates a sense of ease and allows everyone to enjoy themselves (which is the whole point) is for everyone to pay for what they had, so that nobody is sitting there fretting about sponsoring someone else’s third glass of prosecco. I can definitely recall many group dinners when I was younger that were sort of ruined for me by wondering what the grand total was going to be (and, back before Venmo, who was going to underestimate their contribution).

TL;DR the right way to do it is the way that lets everyone focus on the experience more than the money.

Lizzie: YES. I will also say that at least in some groups I have been in, sobriety comes into play. I went on an amazing trip for a friend’s 50th a couple years ago, and several people on the trip did not drink. And we wanted to make sure that the nondrinkers didn’t have to pay for the Sicilian wine the rest of us drank! So what we did was …. everyone entered everything they spent into SettleUp (which was kind of a pain in the beginning tbh). But at the end it was like “Lizzie you pay Anna X amount, Anna you pay Nancy X amount” … yada yada. Again, this was a group of professionals who had undertaken a trip together, realizing that there would be a decent outlay.

One rule I will stick to is “Hey how do we want to pay for this” is a conversation best had at the beginning of the outing. Or even in the planning process. Because that way you do not end up with someone who is barely making rent this month stuck in an awkward moment at the end of a meal! “Hey, if things are tight, let’s go for a walk in the park instead,” works beautifully.

Oh, I also believe that the birthday person in a group dinner shouldn’t pay. They can (and maybe should?) offer. But everyone else should cover them.

Jenée: Lizzie O’Leary, queen of tackling awkward scenarios with direct conversation, strikes again. It would not ever have occurred to me to utter, “Hey, how do we want to pay for this” but that’s so very smart and so much less emotionally draining than leaving everyone wondering what might happen.

I agree with the birthday dinner rule but (yes, like I said, I follow these social media debates closely), I also know that in some cultures and places the birthday person traditionally pays for everyone else.

Lizzie: Oh damn, I did not know that! I mean, I am sure that some people would consider me very gauche to bring that up at the start of a meal, but whatever. As you know, I am 50 and full into my “This is who I am, deal with it” era (with reasonable caveats apply of course). I am pretty sure I did not pay for my surprise 50th birthday dinner. My last thought is: If you can afford to be generous to your friends, go for it! I have one college friend who did very well in tech and he surprised a large group getting ready to Venmo each other by just … paying the whole thing. Not in a showy way. It was a genuinely kind gesture.

Jenée: Absolutely, if paying for everything causes zero stress for one person and eliminates what would have been a little stress for everyone else, under my rule, they should pay. In next week’s episode of Timeless Money Questions with Jenee and Lizzie: Do you have to buy a wedding gift if you spent thousands of dollars on pre-wedding events and your hair and makeup? I say no way! Again, unless you’re super rich. But more on that another time.