Ask Philip: The ABC's of splitting the check

Dear Philip:

My friend Eve is financially well off, but never picks up the check when we go out. She doesn’t offer, and when she’s asked, she insists on paying only her share, which she calculates ruthlessly. She has no problem letting me or anyone else pay for her, though.

Ironically, Eve brags about her family’s money and extensive art collection, and yet is a total cheapskate. This weekend, she let me and a few of my friends buy rounds, but when it was her turn, she handed the bartender enough money for her own drink, and then left. Out of embarrassment, I picked up the rest of what should have been her tab, and made excuses for her.

How do I get Eve to see how awful this makes her look?

Feeling Taken Advantage Of

 Dear Feeling,

Why on earth do you assume Eve cares how she looks?

It’s a rookie mistake, Feeling: because you believe in fairness and sharing and the other basic tenants of conducting a friendship that sometimes involves pulling out your wallet, you take for granted that those beliefs are shared by the folks you call friends.

Eve is indeed a cheapskate, but she’s also — and this is a technical term — an entitled jerk. If you’re correct, and she’s indeed well off (and happy to brag about it), then there’s no excuse for either stiffing you or embarrassing you in front of your friends. Or dissing you, which is really what she’s doing.

Friendship is largely about mutual respect: You don’t speak ill of your friend, you don’t show up at 7:30 when your friend has been standing outside the movie theater since 7, and you don’t expect your friend to pay for you all the time. It’s not rocket science. It’s also not difficult to spot when someone takes your friendship — and you — for granted.

At the very least, stop including Eve when you go out with others, and if she notices and asks why, explain very calmly that you were embarrassed that she let your friends pay for her, but didn’t reciprocate. Directness can work wonders. If you can’t bring yourself to be direct, then you really need to examine whether you consider this woman a friend, or someone who’s mildly entertaining to hang around with…until the check comes. If she’s the former, the relationship is worth a difficult conversation or two. Otherwise, cut her loose: it’ll give you more time to nurture actual friendships.

Since you raise this specific issue, though, let’s spend a moment going over bill-splitting etiquette. Because it’s an area I’m asked about a great deal, I humbly offer the PVM ABCs of haggling over the check.

A is for alcohol, as in, if you’ve had a few drinks and your companion hasn’t, offer to pay more than half of the check. Especially when there’s wine involved. I’m usually on the other end of that equation, and I can’t tell you how annoying it is when someone orders an expensive bottle and doesn’t take into account the price inequity between a 1982 Lafite-Rothschild and a 2012 Diet Coke. I still usually insist on splitting the bill down the middle, but a fella likes to be shown common courtesy, you know?

B is for blood — as in relatives. The generational picking-up-of-tabs is different in every family. We grow up with our parents paying for everything, and some parents insist on doing that long into our own adulthoods. It’s okay to offer in such situations, but it’s not okay to insist: if your mother and father take paying as a point of pride, let them. And then be effusive in your gratitude. I’ve managed about a 5% success rate in paying for my father’s meals when we’re out, and if you know my father, you’ll be impressed by that.

C is for calculators. Don’t use them, and don’t hang out with people who do. Nothing screams cheapskate like someone trying to figure out the exact difference in price between your pasta and their chicken. Rounding is your friend — and clearly, Eve is not.

Dump her, and take an advice columnist out for a drink, instead.

First round’s on me!


Philip Van Munching is a New York Times bestselling author of advice books, and was a finalist last year in the Good Morning America nationwide “advice guru” search. Email your questions to [email protected]



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