At the Stork Club, 1950. Who's paying for Hemingway's drinks? (Getty)

In my early twenties, I was making a pittance while most of my local friends were working in finance earning bonuses bigger than my annual salary. They went out to dinner a lot.

I never really joined them at these group dinners, and they would often get frustrated, and thought I didn't want to hang out with them. It caused some tension in our friendship, and I missed out on that kind of conversation that unfolds over long, lazy dinners. I do remember joining them once, for sushi, and it felt like I was a kid peering into some adult world that came to life when I wasn't around.

The check was split evenly at the end of the night, and the fantasy world I had been living in came to a crashing halt. Even though I didn't have any sake (it's always tasted like pins and needles to me), and I only ordered a cucumber roll, I was expected to hand over the same amount. I probably owed about $18. The bill was was in the hundreds. The night was fun, but that still didn't mean I had almost $100 to be a part of it.

If we lived in a world where it was universally understood that everyone pays for what they order at group dinners, during those years I would have been able to spend more time with my friends—laughing and catching up, living life, building memories. But, somehow, sharing a meal with friends can be much more complicated than that.

This week my colleague Nell Casey wrote an essay on bill-splitting that concluded "everyone should just split the bill evenly. Yes, even if you didn't drink. Yes, even if you are allergic to avocado and the table ordered pricey bowls of $26 guacamole. It's the easiest thing to do and the right thing to do." If you can't afford to do that, then you should stay home, she says.

Casey explains that "anyone organizing a restaurant meal should be cognizant of other people's budgets and understand that it's not going to be a fit for everyone at all times." But sometimes even the best of Friends don't do this... (sorry).

And this line of reasoning isn't always realistic. Group dinners aren't just pre-planned birthday meals, they're often on the fly, where you may already be out with a group—in these scenarios, do you know everyone's financial situation? The fact of the matter is that there's no hard and fast rule here—what will typically happen is that everyone will quietly assess the situation when the bill arrives and if someone has ordered way more, they will offer to pay more, or leave the tip.

For more on this, I reached out to the some friends I've dined with. I told them my colleague had written an opinion piece on bill splitting that I disagreed with, particularly the premise that everyone should split the bill evenly during group dinners, no matter what. Even if you just ordered a slice of tomato and a warm glass of lemon water. My general take on this, I explained, is that even splits are fine if it's "close enough," but if there is a huge difference because your friend ordered a $100 bottle of wine and the lobster, and you got a water and side salad, then some more complicated math is necessary.

My friends agreed, which is why we remain friends that can dine together, and some had some alternative tips should you find yourself in this scenario.

  • "I recently (mostly) quit drinking, and picked up this solution from someone with whom I've dined. If one member of the group consumes significantly less than others (due to not drinking at all, or not ordering an entree, etc), the bill is split but that person doesn't leave a tip. The others split that person's tip amount between them. The person will still get screwed, of course, but less. At least it's something! Under no circumstances should everyone put in, in cash, the amount they think they owe, and leave it up to one person to pay with a credit card, as that person will always get ROYALLY FUCKED. I would rather all my friends get food poisoning than be that person ever again."
  • "One person should pay with one credit card for everyone — frequent flier miles — and then everyone should Venmo that person what they believe they owe. And if the person who paid for everyone sees that someone Venmoed them less than they should have, that person is kicked out of the friendship group!"
  • "I think there's a general policy of fairness (or ought to be, anyway) — if one diner orders a much more expensive meal or drinks, then that person ought to be self-aware enough to insist on NOT splitting equally and paying for more of the bill. Or at the very least, taking care of the entire tip."
  • "Friends shouldn't be too troubled over an extra $5 or $10 spent by a member of their party. But if someone is having 4 beers while everyone else has 1, your friend should be able to handle some good-natured shaming. 'Hey you're gonna tip more for us, right Daddy Warbucks?' This works!"