From mind-blowing bridezillas to caviar-eating kids, these shocking stories reveal how the ultra rich really are different from the rest of us. And not in a good way.
1. The Oldest Trick In The Book
I work in a VERY nice steakhouse. As in, most people’s eyes would pop out if they saw how much our steaks cost.
One time, this gentleman ordered one of our nicest cuts with all the trimmings. He devoured the entire thing—then called the manager over insisting he “didn’t enjoy the steak” and should be comped.
I was so relieved when my managed stood his ground. Then the fireworks started. He threw up a huge stink, yelling and swearing about how awful our restaurant was.
He wasn’t winning though. Eventually, he ran out of steam, begrudgingly paid his bill, and left.
2. Air Bud
I used to work for a business that booked private jets, so I have seen first hand the ridiculous ways uber-rich people will spend their money—but one woman takes the cake.
She booked a $45,000 flight…to fly her dog to NYC for dog training. She didn’t even go with him!
3. Good For Dad
My dad works in construction, and he works on some pretty rich people’s houses—but the one guy went a little overboard.
He bought an entire block of houses and tore them all down to build his one, enormous, ridiculously wide house.
It’s so wide that he had a moving walkway installed like at an airport.
4. Abalone Bolonga!
I was a private chef for an actual billionaire. I can think of a million stories, but one stands out. One afternoon, he got a sudden and insatiable urge for abalone. He needed to have abalone. I told him that there was no way I’d be able to get it to the house in time for dinner.
He just looked at me and said, “Oh don’t worry, I’ll get you some”.
Not one hour later, a helicopter lands in the backyard with fresh abalone flown in from San Francisco.
5. New Bed, Who Dis?
I work as a wedding planner, and one of my honeymoon clients insisted that they would not sleep on a mattress that someone else had slept on. So, to make this happen, we had to buy this couple a brand-new mattress for each and every hotel they stayed in. Each mattress cost more than $5,000 and they stayed at five hotels in total.
They would use each mattress for a couple of nights at the most. But here's the worst part. I would then have to make sure each mattress was removed from the hotel and properly disposed of.
6. Best Seat In The House
I am an art student working as a gardener in one of the wealthiest areas in my country. When I start chatting with my customers about my studies, some of them are really eager to show me their art collections. One time I was standing in someone’s bathroom in my dirty gardening clothes while they proudly showed me their 100% authentic Picasso painting hanging above the toilet.
7. A Very Particular Set Of Skills
I went to interview for a nanny job at a fancy downtown high-rise building. I was interviewed by the executive assistant of a divorced dad of two school-age kids whose current nanny had given notice. The job required four overnights a week (when the dad had custody), and I wasn’t super interested, since that meant being away from my cats for half the week and generally disrupting my life.
However, my recruiter really wanted to give them some candidates and I wasn’t completely opposed to the idea, so I figured, what the heck. The executive assistant who interviewed me was a very proper lady in her early 60s. She also clearly had a very close, motherly relationship with her executive boss. But as time went on, it got weirder and weirder.
Among the questions I was asked in the interview was how bothered I would be if I had been told to pack for a trip to Florida, but then had to change at the last minute for a trip to Aspen instead. Apparently, the family had a private jet. One charming anecdote I was told also related to the helplessness of this "poor" executive man.
One time he was actually left to care for HIS CHILDREN overnight when they had the stomach flu. He had called his executive assistant the next morning to say that it was tough, but he got through it—somehow he got through it. The woman interviewing me seemed to find this quite endearing, since she told me the story with the smiling fondness of a proud mother.
However, she was also simultaneously driving home how very important it was that he had support at all times, and this is why the job required so many overnights. At the end of the interview, as she was walking me to the elevator, it somehow got more uncomfortable. She made a snide comment about the fact that I had worn jeans to an interview.
She said decided to overlook it because of the weather. So yes, we had had a snowstorm the night before and the streets and sidewalks were still slick. I was also wearing new, dark skinny jeans, a cashmere sweater, jewelry, makeup, and boots that would keep me from slipping but still looked nice. BUT I also always wear clothes I can play in to nanny interviews.
You never know when they are going to spring children on you for an impromptu audition. Also, it is a nanny job, not an office job. One where you are expected to cook, clean, and most importantly play, so you really shouldn't be dressing up in an executive suit. But whatever. In the end, they interviewed many candidates from multiple agencies across the city.
The only one who got called back was a girl who actually got to meet The Man. He liked her and asked her back for a second interview, and then a lunch interview. They strung her along for weeks and she turned down at least one other job she was offered, hoping for that one. After all that, their current nanny decided she’d do one more year after all and that was that.
I was so glad I didn’t make it to the next round of interviews.
8. More Dollars Than Sense
There was a bar I used to go to that did quarter nights where you would order something from the bartender and then you would flip a quarter for it. If it came up heads, you only paid 25 cents. If it was tails, you paid the actual cost of the drink you ordered. Anyway, I met these guys who would keep ordering whole bottles just for the fun of flipping a coin.
When they got tails they would all stomp their feet and pay up. When it was heads, they would all cheer, pay the quarter, and then tip the amount of the original bottle. These bottles were well over a few hundred dollars and they did it over and over all night. They just liked the thrill of flipping the coin. The bartenders loved them.
9. A Deck Too Far
There was this guy at my university who was super rich and had a new car pretty much every semester. During his final semester, he went in to dispute a $30 parking ticket for parking in a spot reserved for faculty. He did this because he wanted to park right next to the building instead of at one of the big parking decks, which were a 10-minute walk away.
Anyway, this student’s defense was: “I park in faculty spots all the time and pay the fine, I know how it works. This time I actually wasn’t in a faculty spot”. So the admin looked up his record. This is when the bottom dropped out. Apparently, over the past four years, he had been given more than 300 tickets for parking in faculty spots.
More than that, all of them had been paid immediately. The guy’s philosophy was basically just like, “Nah, screw it. I’m not walking. I’ll just park in a professor’s spot and pay the fine every day”. Strangely enough, they did end up waiving the single fine that he had gone in to dispute, and I think he probably was right that it wasn't a faculty spot.
10. Queen Of The Machine
When I was in Las Vegas, one of the casinos I went to had a high-rollers area where you could see part of the slot machine section. These slots were $100 a play. I stood there and watched as an otherwise ordinary-looking older lady played one machine the same way my grandmother played the penny slots. In the few minutes I was watching, she dropped enough money to buy my truck and I don’t think she even blinked.
11. Calling All Cars
I was at a rich guy’s house to service his not one, but two generators. I rolled up to the call box to let him know I was there, and he buzzed me in. As I was heading up the cobblestone driveway, I passed by his garage. I couldn't believe my eyes. This garage was unique in that it had a basketball and tennis court on top of it. Upon closer inspection, I saw that it was basically a mini parking garage.
The dude had 13 cars in there: a Chevy Suburban, Mini Cooper, Subaru Outback, and some other "simple" grocery getters. Then, on the second level down, there were two Bentleys, a Rolls Royce, and a Lincoln stretch limo. This guy took me through four mechanical rooms to get to his generators. We then went back up to where my truck was parked.
While wearing sandals and a Rolling Stones T-shirt, this guy pointed to the right. The he said something I’ll never forget. “If you need to use the bathroom, it’s behind the Bentley”. It was the most nonchalant thing I’ve heard.
12. He Broke The Bank
One of the owners of the company I used to work for was looking at his bank statement one day and saw a bunch of extra fees that he thought were excessive. He called the bank to find out what was going on, but I guess the person at the bank couldn’t explain the fees or was short with him and wouldn’t waive any of them.
In retaliation, he decided to close all his accounts with that bank. This involved paying off the rest of his multi-million dollar mortgage in cash. I was so shocked that he basically had enough cash sitting in his checking account to pay off his full mortgage, but preferred to take out a mortgage rather than pay for his house in cash.
When the mortgage department at the bank realized what had happened and how much interest income they were going to lose out on, they begged him to come back and refinance, but he gave them a hard no.
13. Who Pays The Bills Around Here?
My boss accidentally received a neighbor’s Bloomingdale’s bill in the mail because the store had the address wrong. He didn’t pay attention to the name on the bill and assumed it was his wife’s. He paid that bill for years. He was actually paying thousands of dollars toward his next-door neighbor’s Bloomingdale’s bill without anyone realizing.
When they eventually figured it out, his response was jaw-dropping. My boss was super, super rich, and he simply told the neighbor to consider it a Christmas present.
14. A True Baller
I read that Paul Allen, the late co-founder of Microsoft, had a 414-foot long mega-yacht with a basketball court on one of the decks. Every now and again a basketball would go overboard while they were playing, naturally. So what did he do? He hired a guy to follow the yacht in a smaller boat to pick up all of the basketballs that escaped.
15. Very Petty Cash
I knew a guy who bought a building just so that he could evict someone who was renting space there. Yes, his money was all inherited, and, yes, everybody really hated that guy. He came from generations of wealth and thought that it made him superior to everybody else. I never met the person who was evicted, but apparently he wasn’t “respectful enough” and had to be taught a lesson.
16. One Rich Son Of A Beach
I worked at one of the top resorts in the Maldives as a personal concierge for the elite guests. The ultra-rich and famous would come here for their holidays. Some arrived in private jets, and one family had this super yacht that they kept parked there year-round just so they could use it for the one time a year they visited. But nothing compares to my most ridiculous story.
Once I was told I’d be looking after Mr. Sergei Popov— he’s on Forbes' rich list and lives in Switzerland with his wife and kids. However, the arrival list said he would be coming with a woman who did not have the same name as his wife. So, he arrived in Malé (the capital city of Maldives) by private jet from Geneva. From there, there are several options to get to the resort…
There is a 45-minute speedboat journey for the plebs, a 40-minute yacht transfer for the slightly wealthy, and finally, there’s a seaplane transfer that takes 12 minutes. Popov opted for the latter. So a bit of backstory: I got this job because I speak four languages (Russian, English, Thai, and Mandarin). Anyway, I’m waiting at the seaplane pier for him to arrive for the meet and greet.
They exit the seaplane and I do my usual welcome in Russian. They respond in English. Great. Keeping that distance from us lowlifes. So we get on the golf buggy and I give them the tour of the island and take them to their villa. Even though it’s the second-most luxurious category of villa, they’re not satisfied. So I take them to the only available presidential villa. They like it.
We negotiate an extra $12,000 per night for the upgrade. Their total is now at $27,000 per night. It’s a 10,000-square-foot villa with a lot of bells and whistles, including a private mobile phone with a direct line to me 24/7 until they depart. And so begin the eye-popping requests. His mistress’s 33rd birthday is coming up and he wants me to organize a surprise—money is no object.
Done. He wants a seat at the bar reserved every evening, even though we don’t save seats at the bar. Done. His niece is flying in tomorrow and he needs me to meet her and take her to her detached private villa. When I saw her, I knew immediately what was going on. She gets off the seaplane in a full-length mink coat (even though it’s 100+ degrees) and carrying only a purse and no other luggage.
There is no way this is a "niece". Anyway, his "niece" wants to go directly to the boutique to buy some new clothes. She gets a bunch of bikinis and some other attire that’s more appropriate for a tropical island. I drop her at the villa, but her "uncle" and his mistress are nowhere to be seen. I take her passport and see that she turned 18 just eight days ago.
Nice uncle, I think, getting her a trip to Maldives (just kidding, I was already suspicious). The next day during breakfast, housekeeping calls me to the villa. I walked in and nearly gasped. The master bedroom is a disaster. The sheets were so dirty that they had to be thrown away. Rubbers and bottles were just everywhere.
Anyway, Popov calls me and informs me that his niece is now leaving them. Aww, I was really starting to like this smoking hot bimbo. Now, the mistress’s birthday arrives. I’ve organized a private barbecue at a pavilion overlooking the Indian Ocean that had been specially designed for events like this. I had ordered 100 pounds of rose petals from Sri Lanka.
See, they don’t grow in the Maldives, and I used them to cover all of the sand leading up to the pavilion. Hundreds of candles were floating on the water suspended in transparent fishbowl-type globes. Tchaikovsky was playing. A bottle of grand cru, I forget which, probably Rothschild, was decanting. A personal chef, personal waiter, and waitress were at the ready.
I was on standby. At the end of the dinner, I came to see how it went. He thanked everyone “from the heart”. We thanked him for the $14,000 he forked out for the dinner. Everyone is satisfied. The next day they speak to me in Russian like an old friend. He tells me his departure plan and hands me an envelope containing $2,000—my tip for their seven-day stay.
The total cost of the seven days all in: $230,000.
17. Score!
My friend was able to get a brand new, stainless steel six-burner oven on Facebook Marketplace for pennies on the dollar. Apparently, some rich people bought a summer house in a nearby tourist town and didn’t like the appliances because they were the wrong color. They had never even been used since the house had been completely renovated prior to sale.
18. Them’s The Breaks
This guy cut me off in traffic and rammed into the right side of my car. I was all ready to get angry, to take down his insurance information. But when I got out of the car, he stopped me in my tracks. As soon as he saw me, this guy just handed me a $6,500 check without discussing anything. The damage he caused was only $200!
19. Free Gift With Purchase
I worked at a luxury brand jewelry store, and one time this grumpy woman came in with her husband. They ignored me and walked right past when I greeted them. Undeterred, I followed them and continued to try to make conversation. The woman started asking questions about things in the cabinet. She bought everything I pointed to without looking at the price tag or batting an eyelid.
In less than 10 minutes, she spent more than $33,000. However, once I started gift wrapping everything, she and her husband sat there demanding free things and threatening not to give us business again unless we produced the best, most expensive freebies we could find. The management team literally scrambled to give her a bunch of free stuff—even though $33K isn’t much in luxury retail.
Apparently, every single one of her visits over the years has been big ticket, though, so I guess it all adds up.
20. Breaker High Meets Contagion
At the beginning of the pandemic shutdowns, my friend, who teaches at a private school in DC, had a small group of parents approach her and ask her if she’d be interested in tutoring their children while they all isolated themselves on their yacht in the Caribbean. They wanted her to join them on the yacht and teach their kids five days a week.
Too bad she didn’t end up doing it, but that right there was definitely one of the most lavish ways to spend money I have ever seen to date.
21. Mazel Tov!
When I was in high school (circa 2005), I was invited to the most extreme bat mitzvah I’ve ever been to. I couldn't believe my eyes. I mean, this was a 13-year-old girl’s birthday party but it had a budget of $3.5 million. They had an actual circus tent with seating for 500+ people, and there was a magic show with real elephants and tigers.
They had these animals shipped from Las Vegas to Westchester, New York. There was also a state-of-the-art arcade tent that made Dave and Buster’s look like a joke, full valet parking and limo shuttle service from your car to the main gate of their estate. There was also a gift bag for every guest that included, among other fancy things, an iPod mini. And that was how I got my first iPod.
22. It’s Been A Slice!
I work for a fancy pizza shop and I thought I’d seen it all: orders that cost hundreds of dollars, people coming in from different cities who want it ready when they arrive, etc. Once, I watched a man eat one small slice from each of the 12 pizzas he ordered. He then proceeded to throw the rest of the pizzas out in our garbage bin.
At first, we assumed he was taking it to a party or to his employees. Nope. He just wanted to try every topping combination. He did leave a $100 tip, though, so that was nice.
23. Someone In Cambodia Loves Me
I had this wealthy friend who was kidnapped during his vacation to Cambodia. He had been there for several months and spent most of his time drinking and going to clubs. Inevitably, someone got the idea to kidnap him, and he ended up locked in a dirty shack sobering up while the kidnappers demanded ransom money. It ended with a twist.
Luckily for him, whoever managed his trust was well connected enough to make a few important calls. When a local dignitary showed up with what was basically an army of personal security, the kidnappers let him go.
24. It’s A Small World After All
An international student from my partner’s university bought a plane ticket from Spain to Canada to go to a music festival with some of her friends. She bought it on a Thursday, the festival was the next day, and she would be back home on Sunday. It was a first-class ticket, of course, and there were definitely a lot of digits in that purchase.
“Oh, don’t mind me, I’m just casually crossing the Atlantic to see some friends this weekend”.
25. Spoiled Rotten?
I was working at a luxury hotel and this guy came to stay there with his daughter, who was about six or seven, and her babysitter or cousin who was about 14 years old. Anyway, this guy would stay out all day sightseeing while the two girls were left alone in the room. Did I mention they had lots and lots of cash at their disposal?
The younger girl would order one scoop of ice cream and give the waiter a $50 tip. Then she’d call again 10 minutes later and here we go with another $50 tip. This kept going on and on, so we started rotating the constant room service, and everyone got their share. But still got to the point where it was more than a little embarrassing.
26. Kids These Days
Since moving to a rich town, it blows my mind how so many kids under the age of 10 order the $300 caviar for dinner at the restaurant where I work. One of my favorite customers is a family who does this—they always tip a grand though.
27. Smashed Out Of Their Minds
When I was a bartender, this douchey-looking guy who was probably in his 30s asked me to sell him and his four friends all the champagne we had in the bar. I said no, but I would sell him two bottles and he could always order more when they were finished. He said fine, so I sold him the bottles and then went for my smoke break. I had no idea what he was about to do.
About 10 minutes later, I saw the main guy and his friends running into the street carrying as many champagne bottles as they could. That wasn't the end of it, either. They started smashing the full bottles on the street while screaming and laughing. It turns out my co-worker agreed to sell them our entire stock in exchange for a nice tip, of course.
So there they were, smashing bottles of champagne in the street and then running back into the bar to get more. We managed to stop them and call the authorities, but they ended up taking off in their car before anyone showed up. The bill was crazy, too. Three of them paid $2,200 with their credit cards and one gave around $5,000 cash.
28. Not-So-Fair Play
I was a server at a sports bar that showed all the big pay-per-view events. One night, I had this guy at one of my tables pull out a $100 bill and ask if I could break it into 100 one-dollar bills. I said, “Sure, I guess, but I’ll need my manager to open the safe, and it’s a busy night, so it could take a while”. The guy said that was no problem.
So I brought him 100 singles and the match kept going. Finally, the last match of the night, which was probably some kind of title match, ended. After the winner was announced, the guy threw all 100 of his ones into the air and screamed, “There’s your tip!” It was a really weird way to be a jerk to your waitress, and it took a long time to come to fruition.
29. Bling The House Down
There’s this politician in our area who also has his own shopping franchise. His son is about three years older than me and he always wears about 30 pounds of gold chains around his neck as well as a bunch of diamond earrings and rings. One time I saw him drinking tea at a cafe with his friends, showing off as usual. That was kind of his thing.
When the waiter gave the bill to his group, Mr. Gold Chains took off one of his smaller rings and handed it to the waiter as payment. Then, to make matters worse, he shooed the waiter away like he was some sort of stray animal. It was so disrespectful that it made me sick to my stomach.
30. Miami Vice
When I was in college, the guy across the hall from me in the dorm went away for the weekend and didn’t come back for almost a week. When he finally did get back, his explanation was ridiculous. He said he had been detained by the FBI! Apparently, he had a friend of a friend who was super rich and had flown their group out to Miami to hang out at a suite in the Four Seasons.
It turns out the rich kid, who had a $40K/month allowance, was stealing from his dad’s business to pay for his overages because $40K/month was not enough for him. The FBI had tracked this guy to the Four Seasons and broke up the party.
31. One Person’s Trash…
I used to live near Wesleyan University, which is the college from How I Met Your Mother. Every year when the children from rich families would go back home, the rest of us would go dumpster diving because students would literally throw away working laptops, iPods, and other good stuff. Must be nice to be so rich that you see a $500+ piece of electronics as disposable.
32. Bone Appetit!
I was at a pretty nice restaurant in Mexico City and a guy walked up with two dogs and nodded at the waiter. The waiter came back with a drink and two massive raw steaks. The guy drank his drink and watched as his two dogs each enjoyed a $50 hunk of raw meat. The guy then walked off into the night. Boss move, if I'm honest.
33. A Friend With Benefits
I have a friend, and she and her family are ridiculously rich. I’ll start by saying that they are incredibly nice people and very generous to those around them. They just do not live in the real world when it comes to money, and they forget that other people don’t live like they do. This girl’s mom redecorates their whole house two or three times a year.
This woman doesn’t just replace a few throw pillows either. She goes to extreme lengths. I’m talking all-new furniture, fresh paint, new flooring, new decorative items, and so on. She really likes to decorate for the holidays and every holiday she buys all new stuff. My friend has basically hooked up everyone she knows with full Christmas setups because her mom gets a new one every year.
This family has a bunch of pets, but they don’t take care of any of them—instead they have people who do it. For example, they have gorgeous fish tanks that are looked after by a guy who comes in multiple times per week. They also have a bird room, which is full of multiple exotic birds who are taken care of by someone who comes in every day. That’s not all, though.
They also have a different person who cares for the dogs and cats. And they have a team of people to look after their horses, even though no one in the family rides. When it comes to food, my friend’s parents will get caterers for any old random night. My friend will open her door to surprise catering and there will be so much food that she will have to call friends to come help her eat it all.
Last week I went over and had dinner with her because they had a full prime rib dinner, complete with appetizers, soup, salad, sides, drinks, and dessert for 15 to 20 people—just because it was Wednesday.
34. The Most Magical Place On Earth
I’m an accountant and one of my worst stories involved a business owner who decided to take his entire family of around 20 people to Walt Disney World—and he booked the entire thing as a business expense. When we caught him, we told him that was a big no-no. Not only would he be charged, but so would we, and we would lose more than our licenses.
He strongly disagreed and so we had to fire him, which, I think, is the only time I can recall having to fire a client.
35. Many Unhappy Returns
I have a female friend, over 50, whose wealthy parents advised her to pick out her birthday gift. The price point they gave her was $1,000. So she went to QVC and started ordering a bunch of clothes, shoes, and gadgets—mostly stupid, unnecessary items. She would order a bunch of things, return some, order more, and then return a portion of that.
I guess she thought she was working her way up to $1,000, but after this cycle of purchasing, returning, and purchasing more items went on for a month, she had racked up $11,000 in charges. It got to the point that she and QVC couldn’t even agree on what she kept, returned, and owed. The consequences were actually hilarious.
QVC finally banned her from shopping with them…forever! Her parents were naturally quite upset and finally had to step in and sort it all out. Her father and QVC eventually settled on an amount somewhere between $5,000 and $11,000. At this point, QVC doubled down on their ban and reiterated to her father that his daughter would never, ever be able to order anything from them again.
36. Sometimes You Eat The Bar…
I was going for a meal to discuss a job with my potential boss. He had offered the job to me at this point and was trying to schmooze me, I think. Anyway, we went to a tapas bar and he asked what I wanted to order. As I was trying to decipher the huge menu and determine how much would be enough, but not too much, he said, “Let’s just order one of everything”.
I was dumbfounded. Unfortunately, I had to return to my home country, so I had to miss out on this incredible opportunity. Honestly, working closely with a man of that caliber would’ve changed my life, but there we go.
37. Read The Room
In college, among our small group of undergrads, most of us drove cars that were worth less than $2,000. One of the guys was from a very well-off family, though, and he drove a variety of $200,000+ cars. One day he was lecturing us about how so-and-so had bad tires and so-and so-is irresponsible for getting a ticket for a broken window on a car he had to borrow because his dad passed.
This guy then went on about how all of us broke college kids need to fix this and that on our cars because it’s only a grand to do each repair. He acted like these repairs are no big deal because he did six figures of damage to a supercar and got it fixed, no problem. I’m like no, we don’t all have a room full of spare wheels and parts for our cars.
38. Champagne In The Butt
I worked at a club in Ibiza, and when you order five bottles of champagne they are brought to you by a bunch of hot girls in bikinis holding sparklers. This meant that people would order massive amounts of champagne just to look good in front of other rich people. Most nights there would come a point where there wasn’t even any more room to put the bottles.
In a lot of cases, they didn’t even drink the champagne.
39. Just Plane Evil
I knew a wealthy guy who had the interiors of two jets refurbished, which included recovering the leather seats. He claimed to notice that the pitch of the hand stitching on some of the seats was different. He assumed that this happened because Cessna had two different craftsmen working on the seats, which was totally unacceptable to him. His reaction was outrageous.
He sent the two jets back to Cessna AGAIN to have all of the seats redone by the same person. On a somewhat related note, this jet owner is the same person who bemoaned that the Affordable Care Act was going to mean his company could no longer kick employees off of medical insurance after they reached a lifetime limit. Yep.
And wouldn't you know it? The savings that this person’s company gained by kicking sick people off health insurance was almost identical to the cost of the refurbishment of the interior of the two jets—nearly seven figures. It was on this day that the cracks began to appear in the conservative rhetoric I had been steeped in my entire life.
40. Sick Burn
I had an adjunct professor for my film class and he always had the best stories. A few of us would often hang out after class and listen to his stories about being a director for many years. When this prof was in college, he had a friend who was a big-time executive. Once or twice per year they would get together for dinner and to reminisce.
His executive friend would always book a really nice restaurant and always paid for everything even though my professor tried to protest. After a particularly good year, the professor insisted that he pay for dinner this time. His friend agreed and when the bill came, it was $12,000. The professor swallowed his pride and went to pay the bill reluctantly.
He was a successful director, but work was not always consistent. Just as he was about to pay, his friend laughed and took the booklet away from him and told him he had already taken care of it. My professor said he would have needed to save an entire year’s worth of pay to afford one day of his friend’s life. Absolutely ridiculous.
41. Insufficient Memory
I used to work at the smoothie counter at an Equinox gym, and there was a man who came in nearly every day. He had the weirdest complaint. He would literally always whine about how he was too busy to remember to pack a gym bag...to the gym. So he would always buy a full set of workout clothes—with shoes—from our retail section.
At that place, a full outfit would run more than my monthly rent. I checked in with the folks in the retail section often and apparently he never returned anything.
42. Money Can’t Buy Poverty
I teach at an international school and we have some incredibly wealthy and well-connected students. Well, during pre-calculus class, we started a topic that is fortunately always relevant: applications of exponential functions and, in particular, compound interest. So I gave my spiel, and one very well-off girl wasn’t impressed at all.
“When are we ever going to use this?” she whined. After I patiently explained why for the second time, she asked incredulously, “But why would I ever need to borrow money?” I sighed inwardly and reiterated my explanation of the power of compound interest with another, exaggerated example. I told her that I could give her $50 now or $100 one week from now.
“Of course I’ll take the money now,” she scoffed. “Why would I wait a whole week for only $50?” Strangely enough, this was also the student who ended up with a UN internship working to combat poverty. This was also the same student who would insult the one student in the class who was on scholarship for being poor. You can’t make this up.
43. Insanely Practical
I had a friend who was living downtown in a major city and needed to buy a car because she got an internship in the suburbs. She’d never bought or owned a car before, but her rich dad wired her some money to cover the purchase. After a few days of finagling with her bank, she ended up filling a bag with $30,000 cash and hopping on the subway.
She ended up at the local Honda dealership. This girl wasn’t a snob, she just wasn’t experienced in these things. She paid cash for the car on the spot, and because of this, she also left the dealership with a new boyfriend.
44. You Had Me At $800 Eyelashes
I had a client who rented out one of the most expensive wedding venues in the city, had designer everything, and generally just spent more money on this wedding than what was necessary. I mean, who cares if your fake eyelashes were $800, seriously. But none of that mattered on the morning of the wedding. That's the moment the disaster began.
Apparently, her mother showed up wearing the wrong shade of green. This bride spent more than an hour screaming and crying at her mother, ruining her expensive makeup in the process, and forcing everything to be pushed back for an entire day. I heard she was fined upward of the original cost of renting the venue and every vendor had overtime charges as we were forced to stay past midnight.
After all of this drama, we later found out that the bride actually never had a job and her parents paid for everything. Oh, and the marriage didn’t even last six months.
45. What A Weirdough
My dad’s a carpenter and one of his clients hired him to build a fully functioning pizza oven in the kitchen of their house. He did. Afterward, while my dad was getting paid for the job, he asked if the family made a lot of homemade pizza. The client said, “No, my wife just needed somewhere to keep the pizza warm when we order it from Domino’s”.
46. Gaming The System
I was talking to this kid and we got into the topic of gaming. He told me his PS4 broke, so I asked him how it happened. He basically said he wasn’t sure, that it just didn’t work when he went to play it. He didn’t seem too bothered by it. But I was about to find out why. He pulled at least $700 cash out of his pocket and told me that his dad gave him money to replace it.
I told him he should at least find out if it could be repaired, to which he said, “Nah, I’m just gonna replace it. I always do”. I realize that it’s not really his fault since he grew up being able to buy what he wanted, but buying a new console on the same day is something my parents definitely wouldn’t do for me. They’d tell me to at least pay $40 to get it checked out first before buying me another.
47. Not A Light-Bulb Moment
I work for an electrical contractor who bills at just over $200 an hour. It’s a union shop that is commercial/industrial certified with journeymen and inside wiremen. The number of customers who call us and pay that price to have somebody come and change their light bulbs is astounding to me. Some people just can't handle real life.
48. Hogwarts And All
One of my colleagues had a daughter who had chosen to get married at a local venue. About three months before her wedding was to take place, this venue happened to appear in a very well-known movie about a certain boy wizard. This set off a bizarre chain of reactions. About a month before the wedding, the daughter had a call from the venue.
Incredibly, they were asking her if she’d move her wedding back a month. Naturally, she said no—all of the invites had been sent, family members were coming from various international locations, and everyone had booked flights and accommodations. It would have been a logistical nightmare to change it all.
But for all that, she eventually did end up moving her wedding back a month. The reason why was mind-boggling. It was because the person who wanted the venue had a child who was besotted with said boy wizard, and their family was extremely rich. This person was willing to do whatever it took to celebrate this child’s birthday, which happened to fall on the original wedding weekend, at this venue.
My colleague’s daughter only agreed to move her wedding after the rich person offered to pay for not only the wedding, the new flights and accommodations, the florists, and the photographers, but also the mortgage on their recently purchased house! The costs ran to several hundred thousand dollars, but to the rich people, it was apparently water off a duck’s back.
49. Literal Helicopter Parents
I worked at a summer camp where a lot of the children attending came from very wealthy families. At the request of some of the parents, the camp installed a helicopter pad nearby so that the parents didn’t have to drive the two hours to pick up their kids at the end of camp. Additionally, many of these parents would give huge tips to the counselors who looked after their kids for the summer.
While I never got any tips because my kids were on scholarship, some of my coworkers were given hundreds of dollars, a Macbook Air, and even plane tickets to come to visit and stay with the families whenever they wanted—sometimes from crazy distances, like flying an Australian to LA.
50. A Fine Mess
During my divorce trial, parking at the local courthouse was a massive pain. Not only was it crazy expensive, but there was also a two-hour limit. I assumed my lawyer must have had special parking privileges. But when I asked him about it, his answer blew my mind. He told me the parking situation was actually just a big racket for the city, and he found a way around it...of sorts.
Because parking was the same for lawyers, his firm decided to just eat the cost of the daily parking tickets instead of having the lawyers go and move their cars to a new spot every two hours. He also said that when the city first enacted “two-hour only” parking, the lawyers tried to comply and move their cars, but they found it to be impossible.
Court is court, things get delayed, and a judge doesn’t give a hoot if you need to move your car. So now the law firm spends thousands every month on parking fines and the city rakes in the dough.
51. All You Have To Do Is Ask
My friend’s dad got a summer tennis membership at this fancy country club because his kid played on the club’s traveling team. The dad got invited to play poker with the other club members on a random Wednesday, and they sat down and decided to order some drinks. The waiter handed the wine list over to one of the old guys and the guy said, “No, show us the real list”.
Sure enough, there was a very bougie list that was only available by special request. Ever since my friend told me that story, I have always wondered what other special privileges exist for these people who know to ask.
52. That’s Mr. Cheapskate To You
I used to work for a billionaire. But this rich guy didn't live how you think. We would go to lunch once a week at a Subway near our office. He would always load up on salt and pepper packages, napkins, coffee stirrers, etc. It was like he took joy in getting one over on the restaurant and getting stuff for free and saving his massive amounts of money.
One time he invited me to a college football game and had me come to his house to meet him beforehand. Turns out, the dude had a seven-car garage full of luxury vehicles. Even so, he insisted that I drive us in my 2002 Jetta with a cracked windshield. He then complained nonstop about my car the whole way to the game and once we got there I bought all the snacks for him and his two sons. To top it off, the seats weren’t even that good.
53. The Upper Crust
I attended private school with a bunch of rich kids, so I have a lot of stories. The best one involved my friend’s sister. This girl wanted a very specific type of bread for her breakfast each weekend—and it had to be fresh. This meant that the family’s servant had to take their private plane to Italy every weekend so that he could bring back fresh bread for her.
54. Super Rich And Rather Strange
I work as a personal concierge at a luxury resort and one night I get a call from my manager as I’m sitting at the staff bar getting trashed. He informs me that there’s a last-minute VVIP friend of the CEO of the entire company coming to stay. There was no time to google this guy. I had a couple of shots for the road and went to change back into my uniform and meet him at the pier.
He arrived just after midnight and in a few minutes, I can tell he is a super high energy eccentric straight out of a Hunter S. Thompson book. Right off the bat, he decides that my name is Dimitry (it’s not). He then tells me that he needs to get ready as his friends are boating over from a neighboring island and he wants everything ready for their arrival.
He needs several bottles of Dom Perignon, a bunch of canapés, and an electrician to install floodlights in front of his villa to better show off the view to his friends. He also needs his shirts to be organized by color in the closet. After he freshens up, he calls me and asks for the villa to be cleaned. So I arrive with housekeeping. I am immediately astounded.
In the bathroom, he has used all of the shower gels, all of the shampoos, all of the conditioners, and there are two entire rolls of dental floss in the trash. Yeah, this man is a mutant for sure. He then tells me to meet his friends when they arrive and take them to the bar to book their spa treatments for the next day. Ok, fine. I go.
His friends consist of three smoking hot babes accompanied by some guy who looks like a cross between Keanu Reeves, Brad Pitt, and Sawyer from Lost. Apparently, he is some big-time Hollywood director’s son. I take them to the bar as requested. Shortly after that, he calls me to say he’s ready for me to bring them to his villa, which is now floodlit and all Dom’d up.
He starts telling the girls about his private jet and joking around that they should fly to Paris Fashion Week on his plane instead of the director’s, har, har. They finish the fun at around 4:00 am. I go to sleep. At 8:00 am I woke up to him calling me with his breakfast order. He asks for an omelet with the works, eggs sunny side up and scrambled, cappuccino, tea, all the fruit juices we have available, bread baskets, fruit platters, cereal, and a newspaper.
I was pretty sure I had already dropped his friends off at their boat, which meant he was ordering all of that food for himself. He tells me to stay and keep him company. Then he proceeds to call who I assume is his personal secretary on speakerphone and starts reciting numbers from a report from memory. He asks why there’s a discrepancy in one of the reports and she throws some guy named Peter under the bus.
Then his friends arrive for their massages and afterward, he tells me that he needs to settle his bill as he will be leaving that evening. I come to his villa to take payment and transport him to the pier. Of course, there are about four housekeepers waiting like vultures for their handouts. He pays for the villa and then looks each of them in the eye, one after the other. I will remember his reaction forever.
He stuffs his hand into his pocket and throws a bunch of bills on the bed. “Dimitry this is only for you”. Then off to the pier we went. Safe travels you weird, weird man.
55. Meat Me Halfway
When I was a waitress, I had a woman and her much younger male companion come into the restaurant where I worked. She ordered a steak with a baked potato. I delivered it to her table and asked if she needed anything else. I was shocked by her reply. She said, “Yes, please cut the steak into bite-sized pieces and put the butter and sour cream on the potato with a bit of salt and pepper, and then you can cut it up, too”.
As I began to realize that she was serious, my smile faded and my jaw started to slowly drop to my chest. Her companion noticed that some not-so-kind words were beginning to form in my brain and he quickly insisted that he would take care of it for her. To this day, I still can't believe that lady had the audacity to ask that.
56. Embrace The Suck
One of my army buddies was a trust fund baby. He actually only served so that he could have the line on his resume since he was planning to go the political route. I’m fine with that as I also served for a line on my resume. However, the amount of care he put into his work was abysmally bad. He would often pay dudes $1,000 to take his duty.
Every few months, he had a brand new Mercedes, BMW, or other fancy European cars. I remember once he ran out of gas on base and just left his car there and went to the car rental place. He then drove the rented car off base to buy a new one. Everyone on our team hated him. So much so that my team leader stuck him in a cave in the middle of Afghanistan.
This was just so he didn’t make fool of himself or get anyone hurt. Last I heard, he was working at the Pentagon. When I went there for work, I saw him and he looked like he was just a secretary. Of course, he tried to make it seem like he was a bigger deal than he was. He literally had people saying, “Hey, guy” because no one cared to learn his name.
But, as I said, everything is for resume points. He doesn’t care about money. He cares about power. He’s a narcissistic jerk whom I imagine will be a very successful politician someday soon because most politicians seem to have the exact personality as him.
57. Where There’s A Will…
My grandfather perished with a $20 million portfolio. He lived in a one-bedroom condo that was built in the 1950s, drove a rusted-out Honda, and his entire wardrobe was over 10 years old and came from Walmart. At the reading of his will, a bunch of distant relatives showed up hoping to get something. I couldn’t believe it when we read it.
First, he ended up roasting them all in his will. Then after he made fun of all of them, he spent 10 pages detailing all of the charities and foundations he was leaving his money to. Some of the info was really surprising, as nobody besides him knew that he casually owned 160 acres of forest in Vermont. The land was donated to a land trust and turned into hiking trails.
58. Hold The Phone
I once worked in the cell phone department at a retail store, and we were supposed to sell a certain amount of phone insurance plans every day to meet our quota. There was this one woman who had just bought four of the latest iPhones for herself and her family. I offered her insurance plans. Her answer sent a chill down my spine.
This woman was so rich, she basically said there’s no point because she would just buy new phones if anything happened. This was in 2018, so four new top-of-the-line iPhones were about a grand each. I tried to push the insurance plans a bit because $4,000 in sales with no insurance or add-ons would hurt my numbers and $4,000 is a huge investment.
So my pitch went along the lines of, “What would you do if the phone broke or you cracked the screen”? That's when it went from weird to terrifying. She got so irritated that she bought four more phones as replacements just to prove she didn’t need insurance. Then she proceeded to berate my selling skills and laughed in my face about being a broke college student working to pay tuition.
I guess she knew this because she must have been eavesdropping on my conversation with a co-worker. I wouldn’t have been upset about any of it up until this point. However, after I finished setting up one of her new phones, she took it to the next level. She went over to a non-carpeted section of the store and purposely dropped it, shattering the glass screen.
She then came up to me and told me to set up her new one. I felt really disrespected, but I had no choice. I couldn’t refuse the request of a customer who just spent $8,000 at our store.
59. Dude Needs To Off-Gas
I knew someone who had a very rich roommate. This roommate would wear a brand new pair of socks every day and then throw them away instead of washing them. You'd think this would make him extra clean or something, but it actually had the opposite effect. Eventually, he developed a rash on his feet from all the chemicals on the brand new socks.
60. The Ghost Trip
If you want to have crazy stories about super-rich people, I recommend being a super-rich person’s assistant! There’s so much insane stuff that I’ve forgotten, but one thing will always stick out.
He had me book this really nice two-week luxury vacation to Europe. The flights, villas, the whole nine yards, bought and paid for. As far as anyone knew, he went on this wonderful trip to Europe, as he often does, to be honest.
I was the only one who knew it was all a lie.
Nobody went on that trip, because he also had me book a trip to Mexico for him and his mistress on a different credit card that his wife didn’t know about.
61. Just In Case
My brother worked on private jets, and a lot of them belonged to Middle Eastern princes. Apparently, they always rolled with these big posses. My brother kinda got to know them. It seemed like everyone had a specific role—except there was this one guy.
My brother couldn’t figure out what he did. Finally one day, he decided to ask. He was NOT expecting the answer: The guy was an organ donor who travelled with the prince at all times in case of emergency.
This prince’s jet also had a full-on surgery room, by the way.
62. Absolutely Disgusting
The snobby old couple next to us flagged down the server during our anniversary dinner at a nice restaurant. They asked to be moved away from “that disgusting couple.”
At the end of the night, the server came over to apologize. I asked her what we did that they said was so “disgusting.” The answer left me speechless: “You two were holding hands”.
I know folks like us don’t usually dine with them in such nice restaurants, but that’s a little much.
