How to Divide the Bill, Not Friendships

I used to throw myself an annual birthday dinner, but I had to suspend it because of hard feelings it was causing among my friends. The bill rarely ended up being fair, because some friends didn't drink at all while others quaffed half a dozen top-shelf martinis. There would always be one person who’d order the most expensive thing on the menu and another who’d have the One-Cheerio Salad, but when the bill came somebody would always say, "Oh! Let's just split it seven ways!" My friends aren't cheapskates (for the most part), but eventually the tee-totalling bulimics who were coughing it up (so to speak) to subsidize bigger appetites cried foul. So, is there an easy way to make group dining more fair? Should everyone be responsible for their own meals? Doesn’t that just lead to embarrassing little squabbles over who had the second Diet Pepsi?

Many a friendship has gone down the kitchen sink over how a restaurant check will be divided. Years ago I stopped going out to dinner with a friend who always ordered the surf’ 'n turf along with an appetizer, dessert, and three to four martinis ($13 each!). He never suggested paying a greater share, picking up the whole tab every once in a while, or even covering the tip. It wasn’t fair, and eventually I realized his behavior said as much about the kind of friend he was as how much he was costing me.

But let me not go all psychotherapy here. Herewith, Mr. Manners gives you the skinny on how to handle the check with friends:

• When eating out regularly with a group of pals, the default is to split the bill evenly. Over time any minor differences should come out in the proverbial wash. (But avoid friends who are gluttons or drunks – for all kinds of reasons.)
• Choose a restaurant that’s within everyone’s reach , which services like Open Table make one-click easy. (Just filter for the number of dollar signs that match your price range.) There’s no reason to further pinch those who earn less or are unemployed and remember this: five-star friends are more important than a five-star dining experience.
• Don’t order the most expensive entrée on the menu, like the obscene $1,000 omelet at Norma’s in New York,  stuffed with lobster and caviar, and then expect your pals who had the steel-cut oatmeal to subsidize you. If you don’t take my advice, then you must overcompensate for your voracity – and by that I mean insist on paying more than the others. 
• Pay attention to what your friends are eating and drinking. Did one of them only have a cup of gazpacho and a glass of house red while the rest of you ordered the four-course prix fixe with wine pairings? If so, the right thing to do is to speak up and suggest that they pay the cost of their meal (plus tax and tip) while the rest of you divide up the remainder of the bill.
• If you’re consistently on the short end of the stick (for example, if  you’re the tee-totaller among heavy drinkers), don’t shy away from saying something like, “I’m more comfortable covering what I ordered,” than paying twice your share.

If you find that those gentle approaches don’t work with your crowd, you can always ask for separate checks – but be sure to request them when you order – it makes life much easier for your server. On that note,  Charlie Deal, owner of Dos Perros in Durham, North Carolina, tells me: "It's a whole lot easier for a server to simply divide up the check evenly than it is for them break it up by who ordered what. Mind you, if you do the math at the table and simply say, ‘Please put $35 on this card, $45 on this card, etc.’ that's pretty easy as well.”

There’s even an app for that. Actually there are many, like Divided Bill Splitter,  which promises to end “strained looks across the table as you struggle to calculate everyone’s total.”  You can do even-Steven splits, make adjustments higher or lower for each person, or decide to pay for a friend.  Last of all, it’s finally cool to be “square.” Square is a nifty little card reader that attaches to most smartphones and allows you to accept payment from your friends’ credit cards while you cover the entire bill with yours. Deposits are made the next day, but buyer beware: There’s a 2.75% fee per swipe and that comes out of your back pocket.

Finally, I have to address the issue of your throwing yourself a birthday dinner at which you expect your friends to foot the bill. Mr. Manners cringes at the idea of “guests” paying for the privilege of attending your party. If you insist, be sure to let your friends know in advance that they will need more than mad money for the evening.

This column originally was published on Advocate.com.