Are you a check-splitting ninja?

The smile on the face of our waitress at Universal CityWalk’s Margaritaville seemed to slip when, at the end of our meal, my girlfriend said, “Separate checks, please.”

I couldn’t blame the server. There were four of us and we’d ordered three bottles of wine and four plates of appetizers over the last two and a half hours.

“Sure, how would you like it broken down?” she asked and suddenly we nervously eyed each other and the piles of platters before us. She discreetly left us to decide.

Splitting the check is an extremely delicate situation. I’ve seen friendships falter, relationships end and business partnerships dissolve over splitting the check. It is my least favorite part of going out with the girls or on informal business lunches and why I almost always insist people come to our house instead of going out.

In high school I’d hung out with future accountants and lawyers, so we rarely, if ever, had an issue with the check. I remember one spring break at college when more than a few punches were thrown over the tip for the pizza delivery.

Why? For some it’s just the principle. “I ordered less and should only pay for what I ate,” they point out. “Someone else invited him; why should I subsidize his meal?” they complain. My favorite is the accusation, “You drank more wine than I did so you should pay more.” And then there’s the fairly common, “That’s a rotten tip, you should put in more money.”

So how can you avoid the unpleasantness in splitting the check?

Be clear before you go

You should never assume you’re being taken out. “Let’s meet at Chili’s,” might just mean let’s meet there and not, “I’d like to take you out for dinner and drinks.”

It’s always a good idea to be very clear during the invitation. If a colleague says, “It’s Christine’s birthday! Let’s meet up at Chili’s after work and buy her a drink,” it’s pretty clear you’ll be splitting the check. This is a great example because you know what will be expected from you.

But that’s only part of the issue. I’ve found what brings people to blows is how the check will be broken down.

Pick your split

The easiest way to break down a check is to divide the total plus an agreed upon tip into the number of people attending. This works best if you’re dining at a family-style restaurant where everyone is drinking the same drink or meal prices are just about all equal.

In other words, this almost never works out fairly.

Remember, your check will be as nuanced and sophisticated as the company you keep. You’ll most likely need a sophisticated strategy to keep everybody happy.

Another split I’ve used I call “The First Round is On Me.” This is especially effective if it’s just drinks and appetizers for a few friends. Everyone puts in his or her order for drinks and I’ll pay the first round. The expectation is someone else will take care of the next round and you’re off the hook.

Don’t try this with larger groups or with people you don’t know well. It’s very easy to be taken advantage of because of your generosity. And that can quickly turn you off going out and splitting the check again — unless you’re a membership-card-wielding points nut, in which case you’ll probably crave the extras the spending will bring.

The fairest way to split the check is to use technology to do it for you. There are apps, like Splitwise, Billr and Divvy, that let you scan the check and in minutes divide the order among the people in your group. Some programs take a little longer to input but also can split specific items like two plates of appetizers four ways and the other plate by three.

Be ready to compromise

In our case, we had been celebrating a birthday. After arguing with our friend – the birthday girl – she let us pitch in for her share of the meal, which we decided to portion equally.

But when we called the server over she surprised us; she’d already gone and broken out the bill.

My girlfriend gasped, but not at the amount. Our server had not only split the check, but she did it brilliantly. She noted that our designated driver was only drinking water and one of the girls was on a restricted diet. Her split was perfect.

Let’s just say we left her an excellent tip. But as we departed the restaurant I couldn’t help but ask her, “How’d you do it, and so quickly?”

She winked and said, “I used an app on my phone.” I wish I’d asked which app that was!

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