19.06.2025

A gentleman's guide to managing friendships

A gentleman's guide to managing friendships when financial habits clash. Learn how to set boundaries, maintain respect, and preserve lasting relationships without compromising your values.

Words: Byron Tully

Bon Zainal & friends.

Photo: Bon Zainal menswear

 

Recently, I received an email concerning what I’ll call “the management of friendship.”

The sender’s inquiry went something like this:

I have a couple of longtime friends whose company I enjoy. However, they aren’t as attentive to their finances as I am. When we go out for dinner or drinks, they order and spend without regard to price. Inevitably, their portion of the tab ends up being larger than mine. Still, there’s the expectation that we’ll either split the bill evenly at dinner, or that I’ll pick up a round of drinks, even when I’m not drinking as much as they are. How can I handle this without offending, but still not spending more than I’m comfortable with?

In response, let me say this: I’m guessing you and your friends are probably at the same income level, more or less. I guess this because affluent people will sometimes pick up 100% of the tab when they’re with less fortunate friends and simply say, This one’s on me, guys. They’ll do this without making a big deal about it, and also without doing it every time, so no one feels uncomfortable. It’s just a way of being fair, of being a friend.

If everyone is affluent, one person will often just pick up 100% of the bill, and the group will rotate, with each member picking up the tab on a regular basis. This is done for the convenience of the waiter or bartender, and for appearances’ sake: doing the math of who owes what in a restaurant can be tedious and tacky. Just pick up the tab and accept thanks, or settle up in the parking lot.

Douglas Lim, Raj Aria, Bon Zainal, Jehan Miskin, Resh, Sha'arin Razali Wong

Photo credit: Bon Zainal menswear


Another option is to address the issue directly. This should be done diplomatically but unambiguously. If someone orders an expensive bottle of wine or numerous drinks, don’t partake. Limit your expense to appetizer, main course, and dessert. Know exactly what you’ve spent.

When the bill for dinner arrives and someone suggests splitting it evenly, you can then respond by saying “I didn’t have that much, so I’ll just cover my meal tonight.” Then pay for your food,  add in a fair tip, and leave it at that. Your friends should get the message.

If they don’t, you can opt to limit your socializing with them to coffee in the morning or an economical all-you-can-eat Chinese buffet. Either way, you probably won’t mind picking up the whole tab without that much thought.

The reality is this: friendships change over time because people change over time. Sometimes our friendships fade with time and distance. Sometimes they flourish, wane, and return. Family we are born with. Friendships we choose, and we choose to keep them or let them fade.

We’re reluctant to ditch our friends because we have history with them, we can trust them, and it’s not always easy to replace them: any relationship takes time, proximity, common interests, and effort. Furthermore, there are no guarantees that others will reciprocate our interest, or that new friendships will be richer and longer lasting than previous ones.

So we value enduring friendships. We want lifelong friends. Their purity and permanence is comforting, especially in a transactional and temporary world. In order to enjoy these, we have to adjust, accept, communicate, and listen.

Note: there may be things going on in your friends’ lives that are making them act carelessly with their money. (Extravagance is the fear of poverty.) So don’t pry, but be aware.

Don’t be harsh, but don’t let this slide. It can create resentment. Also, this kind of behavior on a regular basis might be a signal that these friends aren’t really as genuine as you think. Take inventory of how often you’re out of pocket, and how you feel after spending time with them.

It might be time to see them less often after reconsidering why you’re actually friends with them in the first place. There may be a person in the group who shares your concern, and you may be able to speak with them about the issue to get some clarity. Just don’t gossip. Don’t say anything about your friends to one person that you wouldn’t say to everyone involved, face to face.

Know that this isn’t something you’ll have to do just once. This kind of reflection occurs not often, but regularly, as you assess the role of friends, colleagues, and family members in your life.

Note: if you’re socializing with these people for career advancement, this might just be part of the price you pay to get what you want. Weigh it. You may achieve your desired goal. You may only get used.

Know that you’re going to learn a lot about your friends when you tell them, Hey, I’m trying to budget my money because I want to buy a house in the next couple of years. True friends will support your choices as you try to reach your goal and adjust their free-spending ways when they’re with you. They’ll be mindful of how their behavior impacts you. It’s called being considerate.

A disregard of your reasonable wishes is disrespect. And it’s better to be alone than to endure disrespect.

Nevertheless, the end goal is to experience the best of life…with the best of friends.

Contributor

Byron Tully (right)

Grandson of a newspaper publisher and son of an oil industry executive, Byron Tully is an author who also writes for the entertainment industry. His nonfiction debut, "The Old Money Book," was published in April of 2013 to excellent reviews and enjoys consistently strong sales worldwide. His other works include "The Old Money Guide To Marriage", "Old Money, New Woman: How To Manage Your Money and Your Life", and "Old Money Style - The Gentleman's Edition".

Byron regularly contributes to its blog, www.theoldmoneybook.com, which has been visited by over 1 million readers since 2014.

In February of 2020, "Old Money Style - The Gentleman's Edition" was published by Acorn Street Press. This fourth book in the Old Money series reveals the fundamentals of dressing well in a classic and timeless style. In November of 2020, Byron published a 2nd Edition of "The Old Money Book", which expands on his original classic. This 2nd Edition includes vital information and insights for readers as they navigate a very different, post-pandemic world.

Byron speaks frequently about the culture and values of Old Money. He has been interviewed by KABC New York's Financial Quarterback Show, The Huffington Post, and The Simple Dollar, among others.

He lives in Paris and is happily married to an Old Money Gal from Boston.

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