How To Plan A Trip Or Dinner With Friends Of Different Income Levels

Financial disparities can make trip-planning and dinners super stressful. Here's how to be more accommodating of all your friends.

Over the summer, a TikTok post from investor Tom Cruz made its way to Twitter, where it went viral. In the since-deleted video (it’s preserved on Twitter, though), Cruz details how he and his fellow rich guy pals plan their luxury vacations.

In the clip, Cruz shows off a spreadsheet that outlines each friend’s respective incomes ― his top-earning friend makes $5 million a year while his “poor” friend, “Broke Bob,” pull in roughly $125,000 a year ― their allotted PTO, how much they’re willing to spend on a trip and their gambling habits.

The spreadsheet, obnoxiously titled the “Forbes Friend List,” got people talking. Sure, rich-guy antics in general are entertaining, and Cruz was no exception, but there was something else to it, too: If you’ve ever endured the ungodly stress of planning a group trip, you watched the video and thought, “Wow, that’s actually a good idea.”

These awkward moments ― where one friend makes substantially more money than the others or one friend can’t financially keep up ― are incredibly common among mixed-income friends and family members. (Sometimes it’s dinner plans that are stressful. Not everyone can afford to splurge a cool $200 for small plates and multiple rounds of drinks.)

Mishana, a 27-year-old software sales account executive who lives in North Carolina, thought the video was uncouth, but she also got it: She travels roughly once a month (in her off time, she’s a travel blogger) and runs into this issue all the time with her pals.

She’ll start off planning a trip where everyone is game, then watch the group dwindle down to a handful of people as the trip approaches. (Mishana, who asked to use her first name only for privacy, said she makes significantly more than her friends, most of whom work in retail, quality control, and customer support roles.)

“Right before COVID shut everything down, I had planned a birthday group trip to Bali and the group started with six or seven friends and ended with just two of us when it was time to go,” she told HuffPost. (With this particular trip, her friends’ tardiness was also to blame — four people arrived at the airport but two missed their flights.)

Given all the inherent money-related drama she’s dealt with in her time, Mishana is much more inclined to do solo trips these days.

“I also have travel buddies that I travel with that are dependable but we don’t have much of a relationship outside of traveling,” she said.

Openly discuss what you can afford to spend before making that reservation at the pricey new Italian hotspot in your neighborhood.
d3sign via Getty Images
Openly discuss what you can afford to spend before making that reservation at the pricey new Italian hotspot in your neighborhood.

Naika, a 22-year-old student in New York, said that on one of her most recent trips, everyone was able to afford the upfront cost of the hotel and flight, but one person hadn’t brought enough cash to do anything but hang out at the hotel. (Naika had done her due diligence and asked everyone what they were comfortable spending prior to the trip.)

“I, along with everyone else, took care of it because we weren’t going to let the friend miss out on dinner or be excluded,” she told HuffPost. “But people on the trip immediately became irritated.”

When the group got back, Naika said she had a heart-to-heart with the cash-strapped friend.

“They told me they were too embarrassed to say they didn’t have enough spending money,” she said. “The thing is, my friend group didn’t mind covering her; the main issue was a lack of honest communication. She never said anything beforehand and it caught us by surprise.”

While it’s frustrating to be the friend who’s called on to spot another, it’s equally hard ― if not harder ― to be the one who feels like they can never afford a trip or a night out, said Daria Victorov, a financial adviser with Abacus Wealth Partners.

“I’ve been very fortunate that my income has noticeably increased over my career but I’ve been in the other situation, too,” she told HuffPost. “My own experiences have led me to figure out ways to make sure others don’t have the same feelings of shame or worry.”

Below, she and other money experts share their best advice for making sure salary discrepancies disparities like these don’t come between you and your besties.

Be transparent about your expectations and budgets right from the start.

Make it a priority to jump on a Zoom hangout or have a cheese and wine night to discuss budgets, expectations and any must-do activities ahead of time. (To make the most of the get-together, encourage everyone to do a little research beforehand, so they volunteer hotel suggestions and restaurant picks. Maybe even start some shared Pinterest boards.)

Be inclusive. Invite everyone you think might like to go, not just the folks you know can financially swing it, said budgeting expert Andrea Woroch.

“This early planning session allows for transparency and helps everyone feel included rather than excluding a friend from the get-go because you assume they won’t be able to afford it,” she told HuffPost. “Throw it out there and let your friends make their own financial decisions.

Early on in the trip planning process, jump on a Zoom or meet in person to discuss each person's budgets and expectations for the trip.
Luis Alvarez via Getty Images
Early on in the trip planning process, jump on a Zoom or meet in person to discuss each person's budgets and expectations for the trip.

Make use of Google docs and, yes, spreadsheets like the aforementioned rich guy.

In-person planning sessions are great, but try to coordinate ahead of time regarding costs and budget in a digital format, too ― for example, private messages or Google Sheets, Victorov said.

“This will give people the chance to respond in privacy and think about it and not commit to something they will regret later,” she said.

Don’t get yourself into debt just to keep up with your better-paid or more well-off friends.

It may be really tempting to say “yes” to every birthday dinner and trip, but be realistic about what you can spend.

“It’s natural to be attracted to things that a friend might have, but that doesn’t mean you should try to keep up with their lifestyle, especially when they’re in a totally different tax bracket,” said Patrice Washington, a public speaker and the host of the “Redefining Wealth with Patrice Washington” podcast.

If you overextend yourself too much, you could easily fall into debt in the long term.

“Much of the debt my clients find themselves in comes from buying stuff they really didn’t need in the first place, like shoes, purses, jewelry, home improvements, trips and expensive cars,” Washington said. “When we work toward getting to the root of why they make purchases they don’t need and can’t afford, those that are honest typically mention a close girlfriend, family member, or neighbor who had something the client wanted.”

If you’re the cash-strapped friend, make suggestions that work for you.

Conversations about income can be extremely uncomfortable, but luckily, you don’t always have to be explicit when you discuss your money limitations, Washington said.

“Even if you don’t want to go into tons of details about your own situation, don’t be afraid to suggest alternative, cheaper hang-out options,” she said. “You can search for the best cheap eats in your town, or get your friends to check out the cool new thrift store you discovered.”

If you know you’re relatively flush with cash compared to your friends, it might be no big deal for you to chip in a little more when the bill arrives.
Vladimir Vladimirov via Getty Images
If you know you’re relatively flush with cash compared to your friends, it might be no big deal for you to chip in a little more when the bill arrives.

Pick up some of the extra costs if you can swing it.

A flight and a $400-a-night hotel room means different things to different people. If you know you’re relatively flush with cash compared to your friends, it might be no big deal for you to chip in a little more so that your cash-strapped friend can make the trip.

“I find that some friends and family who earn more than others may be willing to cover more costs, so discuss this among your group or decide that on your own or among those you know who are in a more comfortable position,” Woroch said. “For instance, on one trip, my friends and I were willing to split the cost of the hotel so that our other girlfriend could afford to travel with us.”

But be careful about IOUs.

It’s great to be generous, but be careful about IOUs among friends, especially if it becomes a habit. You don’t want to create awkward tension with friends who owe you money or vice versa.

“Getting into a regular habit of lending money or borrowing it can create strain among family and friends,” Woroch said. “It’s better to split the bill right at the table or pay for each of your own plane tickets.”

Give friends options and the ability to opt in or opt out of certain parts of the itinerary.

It would be great if trip planning was a collaborative effort, but let’s face it: That’s not usually how it works out. If you’re the de facto planner of the trip ― or that rare type of friend who loves planning (bless you!) ― give your friends a full fleet of options.

Take potential accommodations, for instance. When Victorov is the chief planner of a group trip, she usually picks three options that range in location, amenities and costs, and then gets a feel for her friends’ preferences.

“It’s also worth considering alternative modes of transportation,” she said. “It may not work for all destinations, but if possible, one way to save on a trip is driving versus flying.”

Victorov keeps the activities planned for the trip totally opt-in or opt-out, too.

“I always try to create itineraries with different activities so there’s no pressure for everyone to do everything together and spend the same amount of money,” she said. “For example, perhaps some people would go on a hike because it’s free versus doing a food tour or boat rental, which may cost $100 or more per person.”

If, over time, you notice you have one friend who can’t come on trips and you suspect it’s finance-related, make a point to plan some trips that won’t break the bank, Victorov said. Not every trip needs to be an international one ― even “Real Housewives” casts on Bravo go camping or on weekend spa getaways every now and then.

The same goes for dinner plans. You could continue making reservations at every pricey Michelin-starred restaurant in your city, but do a taco truck and movie night sometimes, too.

Inclusivity is the name of the game here. Making sure everyone in your friend group feels included and considered is worth a lot more than that St. Tropez trip you could always go on separately.

Friendships ebb and flow throughout our lives, but these days, it may feel like all they do is ebb. Friend Zone is a HuffPost series that features reflections on the nature of our friendships and what we can do to maintain and strengthen them — plus, how to know when it’s time to let them go.

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