When you go out with friends to eat or grab drinks, one of the most awkward and uncomfortable things to deal with has to be when the check comes. Especially, when you’re out with friends who are just a bit richer than you. You often times feel the need to cover the check in order to make yourself feel as though you’re not as broke as people think you are. But, other times, you think your wealthier friends should grab this round. It does leave a bit of confusion to some: what is the right protocol when going out with your wealthy friends? Does everyone pay just for their own meal and drinks or is the entire bill split evenly. Well, what if I order just a salad? Should I have to pay for some of your steaks. I didn’t eat it! Lucky for us, the people of the Internet have blessed us with tips on how to overcome this uncomfortable issue especially when everyone is wealthy, expect for yourself.
I recently watched all the episodes of “House of Cards” about wealthy people like the fictional “Raymond Tusk – multi Billionaire” …I found the portrayals very realistic for a change. Their lives are not so different from ordinary middle-class folks. Most don’t drive Lamborghinis, etc. How do I know about rich people? Well, here in Monaco, that is pretty much the only kind of people around: Wealthy people who have moved here and bought a small apartment for a few million Euros…Why? Mainly because their tax savings exceed the apartment costs usually by a wide margin. So most make a million a year or more. I also know a lot of new millionaires from Silicon Valley who live in tax havens like this. They can veer in either direction — big newly rich show-offs who got their lifestyle clues from old movies, or more usually, humble, low-profile guys.
Thus, to answer the question, this is the real “protocol” that usually applies: The person who has invited the other person for lunch at a restaurant pays. Cash or credit card. They don’t have special staff around just to pay bills. I used to always pay the restaurant & bar bill for a prize-winning journalist friend from high school whom I perceived as not having too much dough. Then, years ago, he said “I don’t need you to treat me all the time so we should split the bill from now on.” And that’s what we did after that. Then there was my stock broker and a few others who MADE MONEY from me: They ALWAYS pick up the checks. I never do. I think that is how it works with most wealthy people. If they work for me I pick up the checks. I once had lunch with a guy who must have expected me to pay. I would have — except that he ordered crazy expensive wine at $200 a bottle. When the outrageous “La Addition” arrived, I was not shy & said, “Hey, I invited you, but you can cover the $400 for the wine you ordered.” He actually gave me an argument and claimed to have forgotten his wallet. That was the last time I ever saw that deadbeat schnorrer (i.e. moocher) or wanted to see him.
If invited to dine at somebody’s home, we all bring wine or flowers — usually. That’s what you should do whether wealthy or not. It’s just good manners.
If you go to dinner with someone much wealthier than you are, it is good form to say “Let me pay for my share!” Your host will almost always say “No, you are my guest.” But don’t order the most expensive things on the menu or $200 wine if you expect them to pay. When a consulting client and I go to lunch or dinner & he asks me PT type questions, he pays. If it is purely social & I invited him, I pay. Sometimes we split. No special rule.
“The very wealthy, especially old wealth or “old money” as it’s sometimes called, have a set of protocols as second nature to them as splitting the bill is to us. The ones I have glimpsed are as follows: They have an arrangement with the establishment, whether it’s an exclusive restaurant or Harrods. At the restaurant there is no bill. It is just handled.”
“I’m not super wealthy, myself, but I have friends who are. And my answer is a little counterintuitive. They usually pay. But it’s not because they’re rich – or, at least, not directly so. It’s that they reach a point where money isn’t a big deal, so they don’t like to waste time and energy on these issues. I.e. “Let’s get the damn thing paid, and let’s get out of here.” Or, by the same token, it’s totally OK if someone else wants to grab the check quickly and without fuss or drama. Just as long as it’s not a Thing. “
“I eat out almost every day. Often twice a day. It’s either that we trade off: I buy one time, the person that I’m meeting with will buy the next. Or…If it’s someone that’s not as well off, even if they are asking for mentoring/advice, I pick the restaurant that I want to meet at, so I almost always pay.”
“Hell No. What kind of cheapskate do you want to be seen as? I figure that I make $2,000 per hour in passive income so as long as dinner for 4 or 8 or 12 isn’t $2,000, I figure it is no big deal. I have my own table at restaurants that I frequent. I have a saying “My table, my rules”. I almost never let anyone who is my guest at my table pay for dinner. I have allowed a few notable exceptions when the person invited me to dinner and they insist for whatever reason. I never split a check, I haven’t done that in 30 years.”