The Moneyist: I want to treat my friends to dinner, but they keep spoiling my fun

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Dear Moneyist,

I’m from Ireland where we value hospitality highly. I’ve now found myself in a situation with more than one person where we fight to pay the bill. I’d say I created this dynamic because I love to treat people. It started because I currently live in a small apartment so I can’t have dinner parties (although I occasionally cook for one friend at a time, or have a few people over for a meal on their laps).

So when I’m out for brunch, lunch, supper or a coffee I like to spring for my friends. But now they know I’m going to do this so they try to beat me to it. With some people it’s a game. Sometimes, someone will pay on the pretext of going to the bathroom or get to the restaurant early and give the staff a credit card before the other even arrives.

Also see: The $1 tip is dead

Some of my friends are fine with this and I know they’re not hurting for money. But one friend has complained that this practice of taking turns to treat each other makes him anxious. He doubts he pays more often, but he doesn’t like to feel indebted; he’d rather we always spit the bill, not even in half but by counting the cost of what we order.

I find this kind of joyless. But I wonder if other friends on a budget would prefer we each pay for ourselves? Have I involved them in an expense they would rather not incur? Have I put them under a compliment? It wasn’t my intention. But I see now there are pitfalls I didn’t anticipate. What’s the appropriate etiquette for dealing with such a scenario?

Generous diner

Dear Diner,

Thanks for your letter. As an Irish man, I get it. We do “rounds” when we go out for drinks and that can extend to dining out. Your dilemma brings to mind that famous scene from the TV series “Father Ted” — you’re welcome, America! — where two elderly women fight over the bill in a tea shop and, finally, come to blows. They both want to do what they believe is the right thing to do, but there are bigger takeaways that apply to your situation: You want so much to treat your friends, which is a good thing. However, your desire to do something nice has been overshadowed by your lack of flexibility.

There was a time that I thought people who insisted on splitting the bill by itemizing what they had was cringeworthy, but it can make a significant difference, especially for those who either need or like to keep an eye on their spending. Living in a city with a high cost of living (whether it’s Dublin or New York) adds up. Dublin has the 38th highest cost of living in the world (New York is No. 9), according to this ranking of major cities. That puts it ahead of Miami (No. 49), Milan (No. 54) and even Helsinki (No. 62). Basel, Switzerland was No. 1 on the list.

Don’t miss: Meet the most generous tipper in America

I have come to appreciate the attention people bring to restaurant bills in New York and no longer think of them as Grinches. On the contrary, they may be paying less today, but they might also give someone the opportunity to pay less tomorrow. If I order a steak for $35 and my companion orders pasta for $25? It seems opportunistic to say, “Mind if we just split it?” Most people are likely to say, “Sure, no problem” when they mean, “Are you kidding me? Remind me to say I’m busy the next time you call!” The same goes for people who drink wine. Pay for your own at $15 a glass!

I understand your friend who feels anxious about taking turns. They may have enough to splurge one week, but not the next. Especially in these days of freelance work and the gig economy, people’s income tends to fluctuate. (More than one-third of households in the U.S. experience a 25% or more change in their income from one year to the next. That’s a big deal.) Also, taking turns to pay does add more hassle to dining out. We have to remember who paid the last time and, if there’s a long break between engagements, that could leave one party with a bad taste in their mouth.

Recommended: This analysis of 40 million Uber rides reveals exactly how much people tip

Do you have questions about inheritance, tipping, weddings, family feuds, friends or any tricky issues relating to manners and money? Send them to MarketWatch’s Moneyist and please include the state where you live (no full names will be used).

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Hello there, MarketWatchers. Check out the Moneyist private Facebook group, where we look for answers to life’s thorniest money issues. Readers write in to me with all sorts of dilemmas: inheritance, wills, divorce, tipping, gifting. I often talk to lawyers, accountants, financial advisers and other experts, in addition to offering my own thoughts. I receive more letters than I could ever answer, so I’ll be bringing all of that guidance — including some you might not see in these columns — to this group. Post your questions, tell me what you want to know more about, or weigh in on the latest Moneyist columns.

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