Millennials Share The Best Way To Split The Bill When Out With Their Rich Friends

A lot depends upon context and it isn’t always about a person’s wealth.

It’s certainly true that when a person with a big public image invites others to a dinner (without saying more) there might be expectations of some kind.

It’s also true that some celebrities get used to special treatment and some abuse that privilege by not paying when they should.

And there are many do not want to draw attention to themselves. According to “Millionaire Next Door” the vehicle most likely to be driven by an American millionaire, is a Ford F150 pickup.

Then there are those who became wealthy by being careful with money. I suspect they would feel out-of-character if they didn’t continue that behavior whenever there was no reason to do something else.

At the end of it all, the basic premise of this question is probably not right. A person’s wealth doesn’t always dictate who should pick up the check. Aside from birthdays, for example, someone might be returning a favor, or a successful protege might be showing an even more successful mentor some gratitude. As someone once said, “”What’s the point of being wealthy if you can’t do what you want?”

Aside from special circumstances (regarding things like business and one’s public image) wealth brings a certain freedom and the more freedom someone has, the more likely one will pay attention to things beyond his or her wealth.

If Warren Buffett and Charlie Munger (two long-time partners, famously good with money) have dinner together it wouldn’t surprise me if they good-naturedly take turns sometimes , get the numbers “”exactly right” on others, split the bill on occasion, or do something else entirely.

It’s all about presentation. 

A long time ago I was mentored by a wealthy person whose circle included high-ranking politicians, billionaires, and celebrities, etc. Whenever he invited people for a meal, not only did he always pick up the tab, but he also made sure they had the best table, and his guests were seated in a way to have the best view and next to someone they don’t already know well so they can have an engaging conversation.

There’s a famous restaurant in Honolulu called Alan Wong’s. Sometimes President Obama dined there with his friends and family. Surprisingly, aside from security, they didn’t disturb other patrons. Everyone just tried their best to eat and pretend they’re not eating next to one of the most powerful men in the world. I imagine the Obama table didn’t split the bill.

Everything is paid for by the host.

I don’t know which part of he world the top voted answer comes from, but this is how we have done things in my family. And yes I come from those butlers, chefs and chauffeurs kind of family.

When it’s an event. Everything is paid for by host/host company.

I have rarely splitted cheques/bills since I am out of college. When I was in college we took turns and paid the bill. Simple. Sometimes we even splitted for expensive events. We were kids on limited funds. No big deal.

Now, as a grown up man, during formal meets with aquaintances. The host pays. Always. Simple. Without any doubt.

We don’t do fun/social gatherings with acquaintances. Understand that. Everything is formal meet unless with friends and family.

We don’t go and join in others plan.

It’s a switch-off process:

My mother is fairly well off (not super rich, but is very comfortable), and she works in a profession with lots of wealthy people. She goes to a lot of lunches and dinners with her colleagues and it’s fairly simple: she’ll pay one time, someone else pays the next.

It may not be exactly equal, but we’re talking a hundred dollars max – this doesn’t matter to these people.

There are also the people who always insist on paying which everyone accepts and is OK with – they don’t see it as this person ‘flashing their cash’, they see it as generosity.

Still, some believe whoever makes the plans should pay.

As a result of my job, and a few personal interactions I have always noticed a similar pattern when wealthy people go out to eat.

They don’t split the bill.

Now wealthy is a broad term. Someone who makes half a million is also wealthy, and someone who makes a few millions is also wealthy. The people I am about to speak about are from a range within the wealthy bracket.

I have dined with some celebrities, and industrialists (in connection with these celebrities), and I have always noticed that the person who invites the others, pays for the dinner or lunch they have.

It is a matter of pride for the above wealthy person to be a great host, and make sure that their guests have a great time. Right from the chosen place, to the VIP table, to the tasting menu, to the (sometimes) specialized napkins and cutlery, these hosts go all out to make their party or dinner a success.

I remember a time, a film producer hosted a dinner for a few celebrities, some other film people, and some managers (who accompanied their celebrities), and it was a matter of pride for him to take care of everything right till the end. In fact he was friends with the owner of the restaurant that we were dining in, so he made sure that the restaurant was shut to the public for those few hours when we dined there. Additionally at the end, there was no question of a bill as prior arrangements had been made in conjunction with the restaurant owner by the producer who had already offered his credit card details or transferred a certain amount (I don’t know what he did exactly but he took care of it).

So in short, these people pay for the dinners where they invite the others. Whoever invites, pays.

Oh, and in case of a few people making a plan together, each person insists that they take care of the tab, and finally the person who persists the most, gets to take the tab.

Wealth and status shouldn’t determine who pays the bill. 

I am an average young entrepreneur who is bootstrapping a humble business. There’s no investor money, no bank loans, no big lines of credit, and an exhausted personal savings account.

However, I do present myself and my business well. One might assume, from appearances, that I am well off. Not rich, but comfortable. The truth is just the opposite. My wife and I fight every month to pay the bills, we struggle with affording basic things like food (don’t get me started on inflation), and we put off things like Doctor visits because even with insurance, it still costs money we don’t have. But, to someone who doesn’t know us on a very personal level, we look and sound like we do well.

Over the years, through a variety of paths, I’ve surrounded myself by highly successful people who have accumulated wealth. I don’t mean megamillionaires, I just mean they have means. Many of these people are my mentors, my advisors, and my friends. Some are just my clients.

It isn’t uncommon that we will meet for lunch or dinner. In a business meeting, I will always pick up the check, knowing full well that the $100–500ish tab will cost my tiny business a heck of a lot more than their multimillion dollar operation…but I do it out of respect. For personal meals, I will also always fight for the check. I don’t usually win the battle (thank goodness because we can’t afford it), but there have been times where I paid for the meal of a millionaire with the salary of a starving entrepreneur.

What I can tell you is that it isn’t the meals I’ve paid for or checks I’ve argued over that has won me the respect of these people who I admire, though I’m sure it’s just one piece of an overall picture that these successful people have of me.

So, while I may be breaking bread with a wealthy person who perceives me as someone with similar means, which in most circumstances is far from the truth, I will always insist on paying.

Chock it up to the old school southern charm in me, or whatever. I just feel that one’s wealth or status shouldn’t be used for determining who foots the bill.