Everyday People Share The Most Insane “Rich People Problems” They’ve Ever Heard

April 6, 2023 | Christine Tran

Everyday People Share The Most Insane “Rich People Problems” They’ve Ever Heard

“Poor people have more fun than rich people, they say; and I notice it's the rich people who keep saying it.” –Jack Paar

Can a price be put on suffering? Yes, absolutely. And if the suffering soul is rich, well, there’s plenty of pain to go around and be put on credit. When Reddit asked people for their real-life, worst examples of a “rich person problem,” the Internet was more than happy to express their envy. At the end of the day, “more money” did mean “more problems.” If by “problems” one means “God, I wish I had those problems.” Maybe rich people aren’t “just like us.” Get envious as we share 42 stories on the most ridiculous people problems faced by rich people.

1. Always Have a Back-Up Plan

I worked for a gal who had a speaker go out in her Ferrari, and she refused to drive any further under those circumstances, so she pulled over to wait for one of her house staff to bring her the Porsche. True story.


2. Aunt Covert Burn

My rich aunt doesn't let us park in front of her house because it makes her mansion look bad.

Rich People Problems facts John von Sothen

3. Some Things Aren’t Worth the Effort

Girl in college lost $6,000 in Travelers Checks but doing the paperwork to have them replaced was too much bother.

Rich People Problems facts Wemedia

4. Tear$ of $hame

Complaining about your "allowance" from your daddy at age 30 which is the rough equivalent of two average salaries.

Rich People Problems facts Kiplinger

5. How Did They Manage?

When Ann Romney described the rough times that she and Mitt had at BYU.

“We were happy, studying hard. Neither one of us had a job, because Mitt had enough of an investment from stock that we could sell off a little at a time. “The stock came from Mitt’s father. When he took over American Motors, the stock was worth nothing. But he invested Mitt’s birthday money year to year — it wasn’t much, a few thousand, but he put it into American Motors because he believed in himself. Five years later, stock that had been $6 a share was $96 and Mitt cashed it so we could live and pay for education. “Mitt and I walked to class together, shared housekeeping, had a lot of pasta and tuna fish and learned hard lessons.”

I'm sure they really "learned hard lessons."

Rich People Problems facts College Fashion

6. Feathered Foes

My rich friend has had to respray his car multiple times because a peacock on his land keeps seeing his reflection in it and attacking it like crazy

Rich People Problems facts Whats-Your-Sign

7. The “Happiest” Place on Earth

When I was in high school my family was pretty poor, and I had a fairly rich friend. My single dad spent years saving up for us to go to Disneyland. We finally went when I was 16. Fast forward a year, my friend is going to Disneyland for Halloween break. Her dad told her to invite two friends. So, she invited me and another girl. I was freaking stoked. But she kept saying "I don't know it’s probably going to be boring, my grandma takes me to Disneyland like every break." And when we got there all she wanted to do was sit on benches and text. All of the rides were "boring” and she'd already been on them dozens of times. It ended up being pretty boring for me because I didn't want to go on the rides without her.

Rich People Problems facts WSBTV

8. International Fashion Crisis

My cousin's best friend yelled at her dad and said that she hated him because he wouldn't take her to London to buy a dress, even though the exact same dress was available from the exact same store back home. She needed the one from London because "they make things better over there.”

Rich People Problems factsLDNfashion

9. Fly Above the Law

Local billionaire Paul Allen wanted to put a helicopter landing pad at his waterfront compound on Mercer Island several years ago, but the city said no.

So. Paul Allen had a custom-made helicopter landing pad ship built that motors out 100 yards into the lake beyond the city's jurisdiction whenever Paul wants to takeoff or land via helicopter. Zoning regulations are for normies.

Rich People Problems factsFlickr

10. Bought the Right to Be Picky

They bought a new yacht because the wife didn't like the beds.

Rich People Problems factsCharterWorld

11. I Love My Personal Space

Has to buy up all of the surrounding plots of land to get some privacy.

Rich People Problems factsPinterest

12. To Be Fair, It’s Kind of Hard

I had to help a girl pay her tuition bill, she was upset because she genuinely thought the process of putting in credit card information was difficult. Yes, she took her dad's credit card and paid 20k for the semester like it was buying a stick of gum.

Rich People Problems factsMiraculous Ladybug Wiki

13. Even the Rich Pay for Shipping

Superyacht docked in Italy at a high-end marina. Owners wanted the bottled Perrier water for a party they were having in a day or two. They wanted the marina to supply them with a pallet of said water. Marina said it was against policy for them to get a pallet of water to their boat. So, they get a private jet from America to fly in a pallet of said water and get it dropped to the boat. Price was about $28,000 US as far as I remember. But even that amount seems low for that.

Rich People Problems factsImgflip

14. Two out of Four Ain’t Bad

Had a roommate in college from New Jersey, where both parents were very successful lawyers. When Sandy hit a few years ago, he was completely distraught. Their third and fourth beach houses were ruined.

Rich People Problems factsWallpaperstop

15. The Nanny Dairies

I'm a nanny for a rich family. A few examples,

When I get paid (in cash) my boss says, "Man now I'm gonna have to go all the way to the bank to get more cash." Not wanting to go to the bank isn't the annoying rich thing. It was annoying rich thing because he had $500 still in his wallet and it was annoying that he was complaining it wasn't enough money to have in his wallet.

When they travel they prefer two-bedroom suites, one time they could only get a one bedroom and he said, "well that just ruins the whole trip.

My car got broken into and I mentioned it felt so awful to drive it knowing someone was in it. His idea of empathizing? "That happened to me. I HAD to buy a new one."

Rich People Problems factsPanorama

16. The Rich Really Are Just Like Us

I know I'm late to this thread but oh man, I work at a place where I interact with a lot of rich people. I have come into contact with lots of rich people problems. Here are a few I've witnessed:

14-year-old kid looking despondent, and I asked him what was wrong. He replied, "We're going to Paris....AGAIN! I hate it! It's so boring!"

Moms talking, "I took her to her little friend's birthday party, but I didn't know what to bring. Do kids like coach bags still? I have no idea!"

Ladies talking "What are you guys doing this summer?" Second one replies "Oh nothing. Last summer was crazy busy so this summer we are taking it easy. We are spending one week in London and one week in Hawaii, but other than that, nothing. We are relaxing this summer."

Ladies talking: "They can be expensive but buying nicer cars like Porsches and Mercedes is worth it. We had a GMC once and we only drove it for like four years and we had to have something fixed. And it just felt old."

Rich People Problems factsItinere

17. High Speed Wealth

I live in the part of my country where internet is really expensive. 16 Mbps plans are considered plans for extremely rich people. One fine day, one of my friends threw a fit at his dad because he was getting 15 Mbps instead of 16 for like an hour.

Dude, I live on a 2mbps connection which turns into a 512kbps connection after a 30gb data cap.

Rich People Problems factsSafelink Internet

18. The “Fun” in Family Funds

A cousin of mine is on his third Porsche after he wrecked the first two. He told me that his parents said if he destroyed it again, they'd buy him some other car.

He wrecked the first one while hammered, and he somehow didn't injure anyone. I don't even think he got charged with inebriated driving.

My family usually charters our own plane whenever we go on vacation. It costs something like $6,000 per hour or something. One year the company overcharged my dad for a miniscule amount, I think it was like a grand. And he was considering disputing the charge or something, ignoring the fact that $1,000 is nothing to us, and he already paid $36 thousand for a flight.

Oh, and my parents hate tipping the pizza guy for some reason. They have no problem tipping a waiter 50% or even 100% at a fancy restaurant, but the pizza delivery man? F--- that.

Rich People Problems factsSohu

19. The Price of Love

My neighbor is this really down to earth guy who managed to work his way from nothing to being quite wealthy (he has his own company and pulls in north of $200,000 USD per year).

A few years ago, he married this beautiful brunette that can safely be said to be on the upper scale of maintenance cost. She was given perhaps too much freedom when they redecorated their mansion, and ordered custom made stairs that cost about $100,000 USD, which were made of glass/steel.

Once she had them installed though, she noticed that they didn't really match her choice in furniture, so she had a virtually identical set of stairs made that only differed from the last set by a few shades of white.

How this guy puts up with her BS is beyond me.

Rich People Problems factsHomesthetics

20. Adventures from the Other Side of the Railroad

I was pumping gas in a rather dicey neighborhood at a cheap gas station and this older woman pulls up in her Bentley. She pulls up on the pump ahead of me and cracks her window slightly and asks me for help. I ask her what she needs. She asked me to pump her gas because she was too scared to do it herself.

I ask her what type of gas she wanted, and she said the cheapest. I asked her if she was sure, with such a high-end car did she really want to put in budget gas? She said it didn't matter since she could easily afford any new car she wanted. So I insert my debit card and she hands me a $100 bill and says keep the change. I fill up her tank and my own (12-gallon Honda Civic tank) and made about $30 in from the change.

I finish up at the gas station and jump on the freeway to see my girlfriend at the time and I am going the same way at this woman. I get off at the same exit as her she is making a right to an affluent area and I am making a left off the exit to a less nice area.
She rolls down the window and yells at me. I thought you were following me. I am so sorry where are you heading? I told her to which neighborhood I am heading to. She gives an awkward smile and says I will tell the dispatcher that you are not following me and that I am not fearing for my life. She called the authorities on me thinking I was following her to rob her. I ended up getting to my destination chill with my girlfriend and didn't get pulled over.

I work at a hotel and whenever I valet a Rolls Royce or Bentley I just think of this old lady.

Rich People Problems factsPictureQuotes

21. Once You Got It, You Can’t Lose It

My parents are rich, and they grew up super poor. Their rich people problems are constantly worrying about money.

They like to drive nice cars, have nice jewelry, and use it to up their status among their friends. In doing so, they've spent money on useless things along the way simply for the pleasure of others and lost two of their three children claiming that they only loved them for money. It seems when your money is what makes you, you can't believe anyone would want anything to do with you otherwise and begin to treat them that way.

Now they're getting old and have only one of their three children talking to them and that one only does so after having spent about a half million of their dollars on nonsense with hopes that the bank continues to stay open for him. It used to upset me because I didn't want money. I was the youngest, so I just made do with my siblings’ things and I never felt like I was given extra even though we had so much. Then to have your mother call you a w---- when you ask if she'd buy you some running shoes is hard to forget. Especially if they just gave another son 200 grand for illicit substances.

Rich People Problems factsOdyssey

22. Nay Is For Horses (Which I Own)

My dad is a self-made millionaire. He accomplished it through hard work, and he raised me just as toughly as he was (he didn't want me to depend on money).

I have some experience with people of my "status." One girl I know convinced her parents to move, so she could be closer to the horse stables she liked to ride at.

She upped her dad's drive to work, and her mom's, and her little brother had to change schools in eighth grade, the worst time to pull a kid out.

Get this though, she made her mom BUY her favorite horse.

She also would try and make ME buy her a horse, because "I was rich, and I didn't need my money like she did."

Rich People Problems factsPaulick Report

23. We All Suffered

Back when the recession hit, one of my very best friend's family was very distraught, because they had to sell one of their three private jets.

Rich People Problems factsAtlantic Jet

24. Poor in Practice

I worked for a non-profit that helped extremely low-income women start their own businesses. These women would give up food to scrape together enough money to join our program. One of our E.D.'s said she "wished she could relate to our clients more, but she has never been poor." She owned two homes in one of the most expensive zip codes in the US. Also, another woman, whom I really did respect but didn't always agree with, believed people chose to be in poverty. We would debate for days about that statement.

I realized working there that people who run advocacy programs for poverty have no idea what it's really like. This is a problem because policy and law makers are looking at these institutions for advisement on drafting new social safety nets and welfare programs to help the working poor and they just have no clue! It motivated me to go back and get a master’s degree to fight this. I grew up super poor and can speak from experience—not theory.

Rich People Problems factsRessume

25. Settling for Second Best

Drove a client's wife home from the airport after the first big snowstorm in Boston this year. I felt SOOO bad as she told me "Oh, Roger is so sad! They could only clear the snow from in front of two of our garage bays. He wanted to take his BMW out, but he's stuck driving my Mercedes for another week."

Oh. Well how does he go on? /s/

Rich People Problems factsHomeAway

26. Decisions, Decision

Dunno if this is a "problem" exactly but I was on the tube in South London and a bunch of young banker types in fancy suits were there with their equally well-dressed arm candy girlfriends, and one guy was like "Everyone keeps telling me to get a Bentley but I'm more of a Lambo man." This was at a point in my life where I was living off £1 boxes of pasta from Tesco, so it was a bit of a surreal moment.

Rich People Problems factsMake a meme

27. Aren’t They Precious

Young girl—about five years of age getting ready to go into New York City to visit her Grandmother (NJ suburbs). She was at her Aunt's house and did not have a pair of shoes that she liked. She called her chauffeur, told him which pair of shoes she wanted—the dude got the shoes and drove some 20 miles to deliver them and she told him he got the wrong ones and he was an idiot. No one in the family thought this was inappropriate.

Rich People Problems factsPillowfights

28. C’est L’eau

Wife is a flight attendant.

Wife: "What would you like to drink?"

Passenger: "I'll have a water... wait. Where is your water from?"

Wife: "Uh...What?"

Passenger: "What country is your water from? I only drink water from France.

Rich People Problems factsPexels

29. Can’t Argue With That

The movie This is 40.

Rich People Problems factsCollider

30. Why Leave Your House At This Point?

I know a lady who has one of the lifetime first-class passes on American. She has a house in Hawaii and wanted to fly to a city on the mainland, but she doesn't like first class from Hawaii because she had a bad experience one time.

So, no problem she can use her NetJets private jet. But she doesn't want to pay for it. So....

She arranges to make another large donation to her alma mater (she already donated between $10-20 million) and so she calls the president of the university, makes the arrangements, and suggests that they gave an event for this donation. Just so happens, a decent number of other wealthy alumnus live in Hawaii, so why don't they all fly over for the event on a larger private jet, and oh by the way the university should cover the cost of the charter.

I write this in present tense (sort of) because the arrangements are currently being made.

Rich People Problems factsNatalie Off Duty

31. Buying a Head Start

"I didn't start preparing my four-year-old for the Gifted kindergarten entrance exam soon enough and now they have to go private school."

I literally make $120 an hour teaching four-year-olds how to answer standardized questions...

Rich People Problems factsPrivate School Review

32. Relocation Woes

"I have to drive over to my beach house for Internet connection because our fiber optic is being set up today and I wanna watch HBO GO."

Rich People Problems factsOcean Reef Resorts

33. Bank of Dad

I occasionally hung out with a kid whose dad was super rich. He would just ask for money and get it. He tried to use an ATM and had no idea how to, so he asked me or someone else to get money for him. It was so confusing for him. Most simple task were because he was raised not to lift a finger.

Rich People Problems factsPYMNTS

34. Sounds About Right

A kid I know claimed he wasn't rich saying, "I don't get to pilot my helicopter as much anymore." The guy sitting next to him, when prompted to define an income bracket for middle class, couldn't answer. He eventually arrived at a $700,000 annual income as a rough estimate.

Rich People Problems factsSkyfluks

35. Poor You

Not completely rich, but I can imagine it would be worse for someone richer. Cleaning up my parents' estate was a big hassle with safe deposit boxes, bank accounts, rare things to sell all over town. Also, had to deal with clearing out the house and selling it.

Oh, bother.

Rich People Problems factsHonestlymag

36. Duly Noted, Ma’am

My boss complained to me recently that they owned too much land and too many properties, she's like "don't own too much land and properties, it's just a hassle"

Rich People Problems factsHomeAway

37. Never Too Young for an Upgrade

Guy at my high school gets a brand-new corvette stingray for his first car sophomore year. Next year? Sells it and gets a '70s corvette because he thought it was "cooler." This guy is 17.

Rich People Problems factsPinterest

38. Mat About You

I went on an amazing trip (southern USA) with my girlfriend at the time during the summer and she had an uncle who was very rich, and she was used to all his wealth. I was not. I couldn't believe that we got to do all the amazing things we did. Money was just not an object or something you had to worry about.

The third day of the trip I was getting aboard his yacht (he owned the largest one in the club) and it was incredible, glass stairs, stone walls and dark beautiful wood. We all sat down near the back at a table and the wife FREAKED out. She yelled, "Where are the mats?!" Apparently, there were supposed to be "mats" to be set down on the table before the giant glass bowl of chips and freshly made guacamole could be placed in front of us. She was really mad and almost embarrassed.

I've never been so weirded out by someone's anger. I couldn’t believe that it was SUCH a problem I said to myself, "It's fine, seriously I could walk in there and grab them in .4 seconds..."

I'll never forget, and I learned that extremely rich people don't have the same kind of problems that regular people do.

Rich People Problems factsSteemit

39. Breaking Bad

I had friends who "had to break their phone." It was the latest iPhone model and perfectly working but there was a newer one coming out that they wanted, and their parents would only buy it if their other one was broken. I had to endure these kids throwing their phones against walls and being frustrated that their phone wasn't broken yet.

Rich People Problems factsOut Of Warranty

40. A Costly Choice

I was invited to a graduation party, hosted by a very wealthy couple whose daughter had just graduated from Yale. Her father came out, in front of the guests, displaying his Rolex and Cartier watches—asking which one of the two expensive watches the group thought would be "the more appropriate for the occasion." Everyone just looked at each other, silently—not quite sure what to say.

Rich People Problems factsCommunity Wealth Partners

41. Showboating

I was once friends with a Chinese girl whose family net worth appeared to be in the hundreds of millions of dollars. She told me a story about her rich uncle who owned a super yacht and loved to travel around the world. Apparently, his favorite thing to do was pull up into a port and bathe in the stares of everyone admiring his yacht since it was always the biggest one. Well one day he goes somewhere, say the Bahamas, and he pulls into the port and he isn't getting the usual attention since someone else happened to have a bigger yacht then him for once.

This girl said it ruined his whole weekend. He was in a terrible mood and couldn't enjoy anything.

I was speechless.

Also, this is the same girl that constantly complained about how all her friends weren't that smart or nice and how she doesn't know what to do with all her free time and money. That girl taught me something. Apparently, there are a lot of rich people that have so little problems, they just make them up.

And yes, I've seen her Facebook pictures, met her friends, seen her cars, and talked to her long enough to confirm that she probably wasn't lying.

Rich People Problems factsMed-yachts

42. To the Batcave!

I knew someone who traded in his Porsche and bought a new one every year. His parents were wealthy, died when he was in his teens and left him a multi-million-dollar trust fund.

What was sad was that he felt that he couldn't pick up women without flashing his cash and expensive sports car, but he would dump them all in a couple of weeks because "they were only into me for my money." Loneliest guy I ever met.

He is not Batman, by the way. His parents died in a car accident and his butler's name is Davin, not Alfred.

Rich People Problems factsBatman Wiki


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