Look, we'd all love to be rich. Never worrying about money again? Sign me up. But that's just not how it works. Untold riches just aren't in the cards for most of us. But don't worry, there's always a silver lining: We don't have to feel bad about laughing at these god-awful rich people. They'll be fine—they're rich!
1. Born to Spend
I had a classmate in college who was apparently some wealthy diva. Marries a guy whose parents were millionaires as well. Both eventually flunk out and tour the world on mommy and daddy’s account, soon getting married and have a child. They lived with his parents in a mansion at the time. It seemed like a dream, but it was actually a nightmare.
She gets tired of living with them and blackmails her mother-in-law to buy them a house or she will never see her grandchild again. His family refuses. Weeks of tantrums, Facebook and Twitter rants, eventually she moves out...to her own parents’ vacation home...oh, but it turns out she was actually just getting started.
A few years go by, and she is about to get cut off. So she has a brilliant solution: She gets pregnant again then goes back on social media to complain about how her family would abandon a pregnant woman and her child. Her parents crack and continue pouring money in. Husband’s family cracks and buys the home.
Now years down the line, I still see regular social media updates from her about overcoming adversity, triumphing over hardship, beating the odds, chasing your dream etc. etc. The married couple to this day has never worked or gotten a paycheck.
2. Disappear This Miss, Please
I may or may not have carried a heavily intoxicated girlfriend and a large amount of substances out of my boss's house (CEO of a very large company) while she was covered in her own filth so his wife wouldn't catch him as she arrived home from her sister's house a day early. How did this happen, you ask?
My old boss regularly cheated on his wife with any number of women. Well, he calls me one day, because we are friends away from work, and asks me to come to his apartment ASAP. I drive over there, and he's blitzed, and this chick is laying naked in her own filth mumbling about something. He says he has to shower and clean up because his wife is ten minutes away so please "Get that out of here."
I grab the girl and help her to her feet and cover her up with a t-shirt. As I'm walking her out, he yells for me to grab the party bag. The only bag is a Dopp kit. I grab it, jump in my car and drive off. This girl is blasted! She doesn't know where she lives and is sure she's having a heart attack. So, I calm her down somewhat and reach in her purse and find her ID.
Luckily, she has her current address on it, and I take her home. I drive back to my house and pull into the driveway and remember the Dopp kit. I open it up and there's a LOT of illicit substances in there. I got a steak dinner and a few beers later that week from the boss. Needless to say, I no longer work there.
3. 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.
4. 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.
5. 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.
6. Neat Freak
I worked as a valet for about a year at a really classy hotel. We routinely had Mercedes, BMWs, Range Rovers, football players candy colored cars, Porsches... Think of pretty much any kind of high end car and I must have driven one at some point. One time, a guy pulled up in a decent Mercedes, not anything super high dollar. He seemed cool at first, but then he did the rudest thing I have ever seen.
After I gave him the valet claim ticket, he casually went to his back seat and retrieved a newspaper. I was still holding the driver's door open for me and he started disassembling the newspaper. Once he had 4-5 single sheets of newspaper, he began setting the newspaper on his driver's seat, as if to protect it from my apparently dirty self. He didn't even have to say anything, and it was still the rudest insult I had ever received
7. Bottle Service
I was opening a bottle for this table when I started getting chest pains. I was scared because the last time that happened I had a seizure. The pain hit so quickly that I almost dropped the bottle, so I put the bottle down on the table. One lady said: "Honey are you okay?" because it was clear something was wrong. The man who ordered the bottle said "We aren't paying $50 a person for you to die here."
After a couple of seconds—which felt like it lasted forever—the pain gradually went away and I apologized and explained what happened to me the last time. Then the man replied with the cruelest words: "At least you didn't drop the bottle—it costs more than your life." Tears started to well up in my eyes as I poured their drink. I never went back to that table.
The lady who asked if I was okay came up to me later and apologized for the man and gave me a $100 tip. But still I remember feeling completely worthless at that moment. The bottle cost $300.
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8. Overreaction
I worked in the VIP area of a now-defunct stadium. I was in high school and was working a summer job washing dishes. We served various VIP staff including the stadium owner. The owner was actually okay. He even thanked us one time, which was more than we usually got from our guests. His relatives, however were another story...
One day we hear a shriek coming from one of the guests, it sounds like someone was being torn apart. My boss, the head chef, runs out to see what just happened. Turns out there was some dressing on the handle of the label. And one of the owner’s relatives was shrieking like a rat had just popped out of her food!
9. More Income, More Intergenerational Problems
My mom works in a family-owned business, and the owners are extremely upper class. I think the most messed up thing that I know about them is just how they treat members of their own families, let alone strangers. For example, the founder of the company fell and broke his hip when he was around 80.
Since he could barely walk around on his own anymore, let alone run a company, he finally retired and gave the company to his daughter. This was a huge mistake. She put him in a home, never visited him again for his entire life (He passed at age 92, just to give some perspective on how long that was), and almost immediately began to drive the company into the ground.
Around three years after the daughter became the owner of the company, her grandson is hired into basically the same sort of secretary job my mother has. Now it's a bit of a long story, but he lives with his aunt who also works for the company, basically in the same job his grandmother had before she became the company owner.
So, things are going fine for a while, then eventually he comes out as gay, and is immediately fired for some BS reason by his own grandmother. On top of that, she demands that her daughter kick him out of her house or she'll fire her too, but thankfully she wasn't taking any of that, and said she'd sue her mother if she fired her over it. Her mother backs down, and thankfully the kid isn't kicked out onto the streets, but he's sure as heck not getting his job back. Then of course since he was fired, all of the work he was doing is piled onto my mother's desk.
Fooji
10. One Color Too Many
When rich people want to buy a Jaguar in the UK, they get assigned a special salesperson who is incredibly knowledgeable. They meet in a special fancy office, and special arrangements can be made. This was my friend Chris’ job. He had access to things that a normal Jaguar salesperson wouldn't have, like ringing up the manager of the factory for special requests level of access.
Well, a Saudi prince wanted to buy this new Jaguar that had been released, so they met up and spent a full day customizing the Jaguar. The final price was something around 125k for the vehicle. Then came the decision for color. At the time the factory had 16 different color choices for this model. The prince asked if he could sleep on it as it was getting late and it was almost time for dinner.
Chris, of course, said yes and they set a time to meet the next morning. The next morning the Saudi prince said something like, "I figured out an acceptable solution to my color dilemma." To this, Chris asked, "And what would that be?" The Saudi prince's response was so outrageous—it's unforgettable. He said, "I'll order one of each color,” and Chris responded, “Oh, well, of course.”
They quoted the delivery time which was okay with the prince who then asked for his delivery options. On being told about ocean travel options, he asked about air cargo. Chris thought that they could do one or two by air and rest by boat. But the prince said, "No, I want all 16 vehicles loaded on a plane and flown to Saudi Arabia."
So that’s the story of how 16 of the same Jaguar, in different colors, ended up being flown to Saudi Arabia. The total cost was around 2.5 million pounds.
11. Well, That’s Rich
I booked a first-class ticket from Hawaii to St. Louis two weeks ago because my grandmother passed, I needed to fly rather quickly, and it was the only way I could make my travel needs. I get on the flight, and the guy next to me looks me in the face and says “Are you sure you’re in the right seat? You don’t look like you can afford this seat”.
Granted I wasn’t dressed the greatest, but I showed him my ticket and told him to shut his mouth. Didn’t hear a word out of him except “excuse me” the rest of the flight.
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12. Special Treatment?
Flying in and out of DC, we always have air marshals. One time, the agents let them get on early. When the first passengers started arriving, a wealthy-looking older couple came on, and the woman started demanding to know who those men were that boarded before them. Her husband claimed they had paid extra to be the first passengers on board.
This is absurd because we always let wheelchair passengers and others down first. I had the perfect comeback for this kind of nonsense. I calmly explained to her that they were invited down by the captain because they were veterans of the wounded warrior project. That shut her right up for the rest of the flight. I can’t imagine the mindset that allows a person to think they are so entitled they deserve to sit down on an airplane seat before any other person.
13. A Job Well Done
I used to do pool and spa maintenance in my 20s. During this time, I worked on one property with a mountainside, 10-bedroom, 14-bath mansion, with a saltwater pool, tennis courts, guest mansion, and a servants’ house that had four bedrooms and five baths. The property had so much more than this, but that wasn't the craziest part.
For about two years, not a single person was ever there. The middle-aged, single woman that owned it lived in a city about four hours away and just didn't come to the property, because she was so busy with work. A multi-multi-multi-million-dollar compound, just empty. All the time. Finally, after two years, I got a call from my boss on my day off.
He asked if I could go to the house to put some pool floats away. He apologized, because it was my day off, but said the owner would pay me $500 to go put them away. I was confused as to why there were even pool floats out anyway because nobody was ever there, but I figured who cares; $500 for 10 minutes.
I showed up at the house and the woman's adult children were staying at the house with over 10 kids between them all, and they were having a massive pool party/cookout. I awkwardly walked up and said to one of the parents, "Sorry, it must have been a mistake, but I was told to come put pool floats away, but you're obviously here so I'll leave."
But, instead, I got the weirdest response ever. The woman's adult son said, "Oh, no, we're getting ready to leave. You can take them." Then he instructed the kids to push them towards me. I literally grabbed one inner tube float and four pool noodles, brought them 10 feet into the pool house, and put them away. I, confusedly, said they were all set and went to leave.
The son thanked me and handed me a folded mass of $20 bills. It was $400. I was expecting $500 from my boss for payment, but I figured that $400 cash was still overpayment for what I had done, so I didn't mention it. The next day at work, my boss gave me another $1,000. I told him the son had already paid me $400, which was fine.
He said that the son told the woman what a great job I did, so she wanted to pay me $1000 instead of $500, and the $400 from yesterday was a tip from her son. For 10 minutes of work. She actually called my boss the next day to ask if she should reimburse me for gas since it was 15 minutes from my house. I told him that I was all set.
14. The Burden Of Things
My grandfather was one of the wealthiest men in the state. When he received a call, he demanded the phone be brought to him on a serving tray, because he thought it beneath him to get up and answer a phone call. But that's not the worst stunt he pulled. He also legally disowned his daughter because she was seen carrying her own luggage, and the event so traumatized his third wife that she sought therapy for the "disgrace."
15. One For The Road
My dad works in shipping and has a lot of friends who have worked on super yachts. In the 90s, one of his mates got a call up to bring the yacht of a particular Australian media tycoon billionaire from Sydney to New York, with instructions to be anchored in a particular bay at an exact time with a lunch spread for 50 people ready.
So, they got there and set up the food. The guy never showed up. And the reason is so ridiculous—it makes me sick. Turns out that he was having a rich people party in a building overlooking the harbor and wanted to be able to point down and say, “That’s my boat.” He wanted the lunch prepared just in case he decided to take his rich friends down to his yacht, but he didn’t feel like it that day.
So, all the food went bad and they sailed back to Australia without seeing the tycoon.
16. 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.
17. The Fine Print
One of my favorite serving experiences was with a guy who had arranged a big family get-together at our restaurant. I was pretty efficient at waiting tables so they assigned me the whole party, it was probably a couple of dozen people. I was handling it well but the host was tanked by the time he got there and he was complaining that he didn't already have a drink in his hand.
Then he noticed that I was wearing a pair of sunglasses on top of my head (it was an indoor/outdoor restaurant and I was also serving the outside areas). For the rest of their meal, every time I came to the table, he announced how stupid I looked to everyone. The others at the table got so embarrassed that they started to apologize on his behalf.
Our policy was to add a 20% gratuity on parties that big, so when the check came, my tip was already on it. There's a line for an extra tip, which is clearly marked as "additional." This guy grabs the check, looks at me, turns so I can see what he writes, as he draws the biggest "0" and struck a line right through the middle of it so hard he pierced the paper. He turns to me with the most satisfied grin and I just thank him and tell him to have a pleasant night.
The guy is too dense to realize he had already tipped me over $100. My boss and I had a great laugh about it.
18. 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.
19. 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.
20. 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.
21. Excuse Me!
Once I had a job as a cocktail waitress at a bar in Hollywood. It was very "A-List." We served movie stars and celebrities there all the time. It was a very busy Thursday night and I was running drinks back and forth from the bar to the tables. One of my tables had about five glammed up women that looked like they were on a girls' night out.
They were probably in their late 20s and they obviously had money, I could tell by the purses, shoes, and snotty attitudes. I put their order in for their second round of drinks and I'm rushing by their table holding a tray full of drinks including martinis going to another table. The one girl decides she wants to change her drink order so as I pass by her, she turns and grabs the back of my dress to stop me so she can change her order.
Of course my tray tips over when I'm jerked back and the drinks crash all over me and onto the floor. I turn and give her a withering look but she barely makes eye contact and says: "Instead of a cosmo I want a Grey Goose on ice" and turns back to her friends as if nothing happened. I was very tempted to spill some drinks on them next!
22. 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.
23. 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 firm spends thousands every month on parking fines and the city rakes in the dough.
24. 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 bottle 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. 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.
31. Snobette Snootyson
I was on my high school's newspaper staff and we always did a section on cars in the parking lot, where we highlighted one old beater and one super nice car and then interviewed both owners. Everyone loved it—and don't worry, the owners of the beaters were always super excited to be a part of it and they always had the best stories.
So we pick Snobette Snootyson because she's got a nice brand new Range Rover or something, and after I'm the last to call "not it" I'm forced to interview her. I asked her what was her favorite feature of the car? "Well one time I forgot to put it in park and it started rolling away, but it didn't roll that fast so probably that. Or my G-Eazy bumper sticker."
Then I asked, “Got any funny stories about your car?” "Yeah!” she exclaimed. “When my parents first got me it, I was making faces at my friend and turned left when it wasn't a green arrow and totaled it. So they got me the same one again!" I managed to sneak into the article: "Snootyson has managed to keep her car undamaged since October." It was January.
32. Sibling Rivalry
My sister has no job and lives by herself in my parents’ summer condo. She drives my parents old car, doesn't pay any bills, and squanders all the money my parents give her for food and “emergencies” on partying and going to bars. She refuses to apply for anything that isn't a “glamorous” receptionist position for at least 17$ an hour because she's too good for it, despite having a worthless degree from a joke private school.
She has a new garbage boyfriend every other week. She is also incredibly mean. She never has anything nice to say to my parents or other siblings and constantly criticizes them to their faces and behind their backs. The last thing we trusted her with was picking us up at the airport (literally 30 minutes away from the house), for which we gave her a week's notice and texted her every other day to remind her.
We land and she doesn't answer my calls; then she calls my mom to complain and my mother starts yelling at us for “ruining my sister's night.” My sister then sends us a bunch of text messages saying how disrespectful it was for us to ruin her weekend by expecting her to stay home to pick us up instead of going out. It was like 7 pm.
She could have easily gone out after. We had to take the train and it took us three hours to get home. I am never speaking to her again.
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33. 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. My neighbor 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.
34. 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.
35. Your Loss
My wife and I had a gift card for this high-class restaurant that we got as a gift from a well-off friend. So we go to the restaurant and have a lovely meal. But when our meal was over, things went sour. My wife wondered out loud if we’re supposed to pay at the front or at the table. The waitress comes by and overhears us talking about our gift card and she says, “You can give your COUPON to the gentleman over here.”
Then she ROLLS HER EYES. My wife and I felt really embarrassed and we sheepishly left our table. We went to the gentleman at the front, and he was very polite and gracious. I can tell from his behavior that she does this a lot. We left a standard tip to the waitress, but we left the gentleman 25 bucks and the chef 50. Too bad for her!
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36. Childish Dad
I was working a catering job for a 4th of July party at an exclusive yacht club. I went about my business and was clearing used plates from tables. After stacking as many plates as humanly possible, I turn and start walking back to the kitchen. Next thing I know I feel something hit me in the back of the head. It was a chicken bone.
A grown man had been watching me the entire time, with his four-year-old son at his side. Apparently, he decided he didn't want to wait the five minutes it would take for someone else to come by and clear his table, so he chucked his garbage at my head. And then he pointed at me and cracked up. I calmly set down my tray and just walked out of the restaurant without saying a word.
37. Side Chicks
When I was a poor college student my wealthy cousin and his wife went on vacation and offered to let me house sit to give me a break from my three slovenly roommates. They live a few towns over in a very nice house with a huge front lawn and a fancy, tall iron fence with double gates. The fence and gates are about 11 feet high. You have to have a remote to open the gates.
That first night I slept so well! I breakfasted like a king and then drove to school. I got back around five, made a supper fit for a king, and settled down to write an Econ paper. My cousin has a warning system for when someone driving turns off the road and comes up to the gate. There's a chiming sound and you can look at screens in a couple of different rooms to see who it is so that you can buzz them in.
I was deep into my paper when I heard the chime. I was confused at first and check my phone before I realized what it was. I looked from the sofa and could see a movement on the security screen. I stood up and got closer and had a clear view of two women getting out of a white car. One tried to squeeze between two bars of the gate—impossible—and then the other woman tried to boost her over the top of the gate—hilarious.
The top one fell and even from the house I could hear swearing. I was about to press the intercom button and ask WTF was their problem but I was chuckling at their antics and just watched silently. They peered at the house intently from between the bars like a couple of jailbirds for a while. The skinnier one actually stripped down to her bra and panties and tried to squeeze through the bars again. No dice. Chest and trunk were not allowing that to happen. More swearing.
Then, as the skinny one got dressed again, the bigger one went back to her trunk and got out a tire iron. As soon as she started with the hinges of the gate I was calling 9-1-1. The authorities took too long and the women left. I showed the officers the video but they couldn't get a license plate number. When my cousin and his wife returned the next week I told them what happened and we watched the tape. He said that he had no idea who the women were but his wife looked fuuurious. I packed up, thanked them for my "vacation" and left.
She divorced him that summer.
38. 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.
39. 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.
40. 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!
41. 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.
42. 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.
43. 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.
44. 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.
45. 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 nab 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.
46. 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”.
47. Geography Lesson
I worked at this fancy event center where a bunch of yuppies host their weddings. My job was so easy; I literally just opened doors or clicked buttons on the elevator. One time, a man who I had previously opened the door for had come back to talk to me. He proceeded to ask me where I am from and what I thought about him adopting a daughter from Korea.
I am an Asian American, born and raised in the United States, so I responded with something along the lines of: "Yeah that's really cool..good for you." He kept asking me uncomfortable personal questions about living in Korea and made offensive comments. For example, he said the fact that I could fluently speak English was amazing.
The funniest thing is that I’m not even Korean, I’m Cambodian! I told him this, and that Korea and Cambodia are very different places even though they are both in Asia. I come from a very educated and upper middle-class family and in times like these, I literally feel like they think I came straight from the slums or something.
48. 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.
49. 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.
50. 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.
51. 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.
52. Hotel Havoc
I used to work as a front desk agent at a boutique hotel. A guy who was obviously very full of himself came in with an online reservation that he had booked at a shockingly cheap nightly rate. He proceeded to give me a hard time about EVERYTHING, from telling me he shouldn't have to give me his credit card info since he had prepaid his reservation, to telling me "Um yeah, I'm pretty sure I can find the elevators, I'm not stupid."
He was just being an all-around jerk. About 10 minutes after checking him in, he came down and demanded that we give him a bigger room with a king bed and a view, even though he had booked a standard queen bed online. I complied, as we had extra king beds available. 10 minutes later, he came down again to complain about the size of the room.
He told me, "I'm only going to give you one more chance to make me happy," and asked for the general manager. After much arguing between him and my manager, we ended up giving him our nicest suite AND free parking since we had "Given him trouble." He got all this for a way cheaper rate, like $40 per night! Oh, but he outdid himself.
Get this: He informed us shortly after the ordeal, while on his way out to dinner, that he was not even going to be in the room for the majority of his stay, as he was visiting friends and would be staying at their home. What the heck! So I made it my personal mission to make his life a living nightmare from that point on.
I reset his room keys every time I saw him leave the hotel—which was quite frequently, 3-4 times a day. It was particularly funny when he came back tired from a night out and had to come all the way down to the front desk to get his keys fixed. Needless to say, he was very frustrated by the end of his stay. I doubt he'll be staying with us again.
53. 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.
54. 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.
55. 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.
56. 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.
57. 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.
58. 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.
59. 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.
60. 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.
61. 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.
62. 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.
63. 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.
64. 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.
65. 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.
66. 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.
67. 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.
68. 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.
69. Nice Try
I was a host at a local mom-and-pop breakfast place in San Francisco for 7 years. Despite being small it catered to a lot of high-end people like the Mayor and professional football players. So we’d end up with an hour or more wait sometimes on busy brunch days. My favorite thing that people would do is pull the “I know the owner” card to try and get a table. But there was just one problem.
They were totally unaware that the owners both worked the line everyday and were right next to us. So I would respond by saying: “Oh, let me get them. I'm sure they’d love to say hello!” The looks on their faces when the owner would come out and say: “I’m sorry where have we met?” was priceless. It was one of the only restaurants I’ve ever worked at that cared more about their staff than the customer always being right.
70. A Little Harsh
I worked as a waitress at a fancy bed-and-breakfast when I was 20. We hosted a date-night special and it was completely packed with couples. There was an older married couple that was in my section and the husband was super nice. He asked how my night was and even postponed his order so that I could clear a nearby table.
His wife had a permanently angry face and glared at everything I did. After their meals were cleared, it was time for dessert and champagne, as per the date night feature. She orders a brand that technically isn't champagne, it's a sparkling white. I didn't want them to feel ripped off so I told her: "That's a great choice but just so you are aware, this is sparkling and not champagne. Is that okay?'
She looked at me for an uncomfortable amount of time. Her husband is looking at her with an expression of mild concern. Well, her brain must have been going into overdrive trying to think of something insulting, because after a long silence she says the meanest thing: "Sweetheart, I see how hard you're working. Have you considered getting some work done? You wouldn't have to work so hard if you were a little prettier. Just a thought..."
I could not even process what she said until I got to the kitchen. Her husband's face was what made me cry. I can take an insult but the mix of embarrassment and shame on his face just made me lose it. I comped his dessert and made her drink with mostly apple juice. I hope that $27 glass of 80% cheap apple juice was good.
71. 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”.
72. 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.
73. 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.
74. 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.
75. Mind Games
Back when I was a server, there was a woman with a group of friends at one of my tables who asked for a can of Coke. When I brought their drinks and gave the woman her Coke, she looked at me and said, in that typical rich-girl voice,"Excuse me, honey? I asked for Fanta, not Coke." I apologized, wrote it onto my notepad, and went back to get her a can of Fanta.
I brought the drink to her but again she turned to me and said: "I didn't ask for Fanta, I asked for Cream Soda." By this time, I was getting a bit annoyed, but I went back and got her a Cream Soda anyway. Sure enough, when I returned to her table, she did the same thing again. "I asked for Sprite. Should I call the manager?" Oh, honey. She should have stopped testing me when she had the chance.
So, for the last time, I smiled and I went back to the kitchen and packed cans of Coke, Cream Soda, Fanta, Sprite, Pepsi and Sparberry Soda, into a small plastic box and took it all to her and said: "Here you go, miss, take your pick." She looked offended and almost made a scene. She started lecturing me about how I'm incapable of getting the simplest order right and that she wants to talk to the restaurant's manager.
I told her that I can call him, and that I'll show him all the soda types I wrote on my notepad that she asked for, and we can get his opinion on the matter. She turned and took her Sprite out of the plastic box and said "Just leave it." None of them gave me any issues after that!
76. Ahem!
I was a sous-chef at a fancy country club and it was 10 minutes before we opened for the Easter buffet. Needless to say, it was going to be a very busy day. I was walking through the dining room and checking all the final details when suddenly a little girl of about two years old ran into the room. She had escaped from her mom who was at the front desk.
She comes to a stop about six feet in front of us and looks up with her eyes wide. I must have been quite a sight, I was wearing my tall white hat and white apron down to my toes. Her mom appears in a heartbeat, turns her daughter by the shoulder, and whisks her away saying: “Don't talk to them, that’s the help, dear.”
77. Thanks But No Thanks
I worked for the University Mail Services in college, it was mostly just sorting mail but I occasionally helped out with deliveries and pickups on campus. One day I was running the route and picking up mail from one of the admin offices. There was a FedEx package to pick up, and for those, I had to sign the paperwork, note the time, and leave the carbon copy.
I had left my pen in the van, so I asked a couple who were passing by if they had a pen I could borrow for a second. They both looked at me like I'd asked to take his Ferrari for a spin. The guy looked down at his pen and then up at me before handing me the pen in the most condescending manner I've ever seen. Yes, he managed to make the act of handing me a pen condescending.
Then the lady said: "You should ask your boss for a raise so you can afford your own pen."
78. 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.
79. Lead by Example
I used to work in this totally yuppie bowling alley. You might laugh at that, but an hour and a half of bowling and a pitcher is about $90 for two people. I went to check on a lane when a group was getting set up. They were a couple of well-dressed older white ladies with two Asian ~six-year-old girls, both in fancy little kimonos.
I greeted them warmly and asked, "Can I get y'all a pitcher of soda?" And one of the ladies gave me a dirty look and sneered: "You mean you all. I already worry about the girls growing up with an accent, and I don't want them learning bad grammar as well." I couldn’t believe it! She also made the girls practice their 'bow' for me and I was just generally weirded out by almost everything that happened.
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80. Grin and Bear It
I was 21 and bartending in a snooty restaurant often frequented by yachties. One customer commented: "Oh you look about my daughter's age, except she's away at college. A career is really important to her." Little dd they know, I was graduating that year and off to grad school the following year. I just smiled and said, "Wow, that's great. Can I get you another cocktail?"
81. 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.
82. 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.
83. Hitting The Bar
Through past work, I met a guy who asked if I would be interested in some extra bar work at his house occasionally. I said that I absolutely was, happy for the extra cash and change of scenery. So, for the next about four years, I would turn up at about eight, along with a few tools of the trade that I favored, and head through the beautifully disguised secret door.
This led down to what amounted to a self-contained underground house with a fully stocked bar, ice machine, etc., where I would make cocktails for the participants of these periodic "special parties." From about nine, couples, some in little masquerade masks and little else, would arrive and mingle and then vanish and reappear, with a different thirst to quench.
I worked for barely five hours; it was hardly even work. It was an insight into a world I would never know. Afterwards, he came over, fully dressed, thanked me and gave me an envelope with cash. He also mentioned that I may have recognized a few people and that they would appreciate it if that fact remained undisclosed.
I assured him that I hadn't saw a thing, like I was in some terrible movie. My five hours of work made me more than I make in a week. Next day, I got a call, asking if I could come over, just for a few minutes. I was off, so I headed over. He greeted me at the door, brought me into the hall, and said that the guests wanted me to have that, and hoped they would be seeing me again.
It was another envelope with the same amount as before. Every few months for the next four years this was repeated. Until I couldn't do it anymore. I can't describe why, but I would dread the call. I think being part of something that was so throwaway to them while I was living off a bag of change was, at times, just depressing.
84. A Potty Decision
A client went on vacation to France and saw a small one-bedroom one-bath cottage with an earthen roof in the mountains of some village they stayed in. They thought it was “cute and quaint” and bought the cottage off the owner in France. They then proceeded to turn around and have it completely disassembled, loaded into sea containers, and shipped to America.
Upon arriving here, it was completely reassembled. It looked exactly like it did in France. Sadly, they now use it as a “potting shed.” The walls were made out of stone and were, basically, the rocks the farmer had picked out of the field who knows when. Every stone had to be numbered and reassembled exactly like how was in France.
If that’s not the absolutely "no thoughts given about money," I really don’t know what is.
Wikimedia.Commons
85. A Meal To Remember
A cousin works at a branch of a higher-end, world-renowned hotel chain, in a large US city. A couple of years ago, a guy came up to him and asked him for a dinner suggestion and said the price wasn't a concern. My cousin keeps up with what's trendy in the city, knows some owners and such, and gave the guy a suggestion.
The next day the guy asked for him by name, gave him $100, and said that the dinner was amazing. He went on to ask where they should eat that night. Another suggestion and the next day, another $100. Only this time, his manager saw this go down and, a few minutes later, asked my cousin, "Do you know who that is?" He didn’t.
It turned out that he was a well-known old money guy. But that was just the beginning. A couple of months later, my cousin went to work one day and was told that this person would be calling at 6 pm, and only wanted to speak to my cousin. The conversation was short, basically along the lines of "we're in town next month for four nights, book the six of us four wonderful dinners, we trust your opinion."
He was given an email for their family assistant, and to let that person know the plans. The family arrived, said "hi" to him as they checked in, and said they were looking forward to their dinners. Four days later, while checking out, they handed him $1000 "for his wonderful local knowledge."
86. What’s Mine Is Yours
I had a classmate whose father or mother was extremely rich from family money. But they were all amazing people. There was another girl in our class who was really nice but came from a poor family and worked 6o hours a week for three months in the summer. One day, he dropped her MacBook, and my rich classmate came to her rescue.
He just came up, gave her his MacBook, and said he would just get a new one after school and his parents wouldn’t care. Pure generosity. There was no social media chest-thumping going on. He was a stellar dude spending his parents’ money, but only on stuff for other people and in a nice helpful way. He also gave all the guys in class a suit for graduation.
Many of the people were talking about renting and he told everybody he knew a place to rent real nice suits. We all went there and rented a suit each for 100 euros or so, everything included. When we went to return it, we found out they were all paid for by this dude. His thought was that renting a suit is stupid, but buying a suit is expensive and now we had the best of both worlds.
The last thing I heard, he bought about 10 PS5 from scalpers and sold them for retail to kids in the neighborhood.
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87. One Man’s River is Another Person’s Bathtub
I repair bathtubs and showers. I've been in poor homes, middle-class homes, wealthy homes, and super mansions. So, we were at this mansion, the kind where there's a tennis court and pool in the back yard. The kind where the foyer and first room of the house had 16x16 black granite tile with subfloor heating. Just this magnificent house with its three-car garage; but in the garage, there were three lifts to literally stack their vehicles. These guys were loaded.
They are "updating" the house to sell so they can move back to North Jersey. They replaced the soaking unit in the master. The granite in that bathroom was absolutely breathtaking. It was blue, and under a certain light sparkled like there were lights built into it. The deck was cracked at the caulk line. So, we're in there fixing it, being as anal and meticulous as possible because we know we're in probably the most expensive house ever.
The wife comes in to chat with us and basically states that they just got the same kind of soaker as before because it's the only thing that fit in the spot. Eventually, she says something like, "It's okay though, it was only $8,000." If I was drinking something, I'd have choked on it. She said it like the tub was a piece of trash that she settled for because it was cheap. $8,000 was a drop in the bucket.
88. A True Man Child
I had an old friend call me in the middle of the night, begging for me to go pick him up. I thought he had gotten mugged or something along those lines. The actual reason was jaw-droppingly ridiculous. Turns out, he got into an argument with his parents because they bought him a storage space for him to put his childhood items into.
He was so upset that his parents decided to sell their home and move elsewhere to retire and that he would be forced to decide which of his items to keep and sell. I deleted his number right after that night and have avoided him at all costs since then. He is 29 years old and a total man-baby. Like seriously dude, work on your drama.
89. “Stunning Privilege”
I'll throw out the disclaimer that the guy wasn't a jerk, he was okay, but the stunning privilege was both jaw-dropping and hilarious. He was a guy in college who came from a pretty wealthy family. He never had a job before—which isn't that crazy for his age and being a student, though I had been working throughout college.
One day he decided to get a job because he was "bored and wanted to see what it was like." I forget where he got a job, but it was a pretty laid-back part-time job pushing paper in an office setting. A few weeks after starting, we're hanging out, and he's talking about work. He reaches in his pocket and says, "Today they gave me this. What am I supposed to do with it?" It was his paycheck.
I stared at him for a second and said, "Dude, that's your check. What do you mean 'What do I do with it?’ Deposit it in your bank." He says, "I don't know how to do that. My dad just puts money in there. I don't look at it, I just take money out from ATMs or use my card." Not wanting to walk the poor guy through such an easy process, I just tell him to take it to a grocery store and cash it.
What he said next made me nearly fall off the couch in disbelief. He said, "What do you mean cash it? Like, they'll just give me money for this [looking at his paycheck]?" Must be nice.
90. Too Little, Too Late
I was working as a General Manager at a struggling restaurant—struggling despite excellent business, because the owners would do stupid things like take trips to Italy on the company dime to source the "perfect" panini press. They also wouldn't staff properly; I was the only waiter ever there, open to close, six days a week, on top of handling phone orders, inventory, and other managerial duties. I was wildly overworked, but I sucked it up because the base pay was good, plus tips.
However, to fund their lavish "business" trips, costs had to be cut at the store. They decided to do this by bumping me down to minimum wage for tipped employees—effectively cutting my salary to 1/10 of its previous level. They were also too chicken to tell me until I got my new teeny paycheck and questioned the mistake. "Oh yeah haha, forgot to mention that blah blah cost-cutting blah valued team member please work with us through this difficult time."
I had worked for two weeks at this new lower rate without my knowledge. Pretty sure that's against the law, but hey, a lot of sketchy things go on in the restaurant industry. That's not when I rage quit, though....a couple of hours later, I'm fuming and have decided that I can't work for the lower rate, so now I’m just waiting for the perfect chance to give my notice.
They called in a delivery guy who was fired a few weeks before, and they talk about hiring him to start doing our Facebook posts and handing out flyers around town. Whatever. Then I hear them offer him close to my old salary as "Promotions Manager"! What??? I was basically running the place for $2.13/hr and you're offering this dude almost $20/hr to walk up and down the street saying "Eat at (Name)"?
And yet, it gets worse.
They bring up our negative Yelp reviews and this guy suggests asking friends to post positive ones. The boss starts laughing and says "Better not ask our waitress to post one, it'll be all boohoo don't eat there, I can't pay my rent this month because they cut my pay without telling wahhhh!" I don’t think I was supposed to hear that, but I was five feet away, so of course I did.
I RAGED! I quit on the spot, told them to screw their job, and wished them good luck keeping the place open without me. They quickly realized I was right, as neither of them knew how to do more than pick up the takings once a week. They begged me not to quit. They were so desperate that they sat there for half an hour and allowed me to bluntly tell them exactly what kind of huge idiots I thought they were in excruciating detail.
I went on and on as my rage burned, and they just quietly listened, nodding and apologizing. Once I had cursed myself back into calmness, I walked out, 30 minutes before the dinner rush began, leaving them with an unstaffed floor and no clue how to even open the cash register. God, they were morons. I loved that they actually listened to me telling them exactly how stupid they were. No repercussions on my side, as the restaurant industry isn't known for checking references.
The place closed down about 18 months later, and I was surprised it even made it that long.
91. Hitting The Roof
I used to install DIRECTV in wealthy areas of an east coast city in the US. While I tried to give customers options on where I installed the satellite dish, I had to get a good line of sight for it to work properly, so sometimes the location options were limited. At one rich lady’s house—a gorgeous house right on the beach—I only found two good spots for the dish.
It could either be on a pole in the middle of her backyard or on the corner of the roof. She definitely did not want it in the middle of her yard. The only problem was that she had a metal roof and we use specific mounting hardware for that. We happened to be back-ordered on that particular hardware for a few weeks out.
When I informed her of this, she got visibly upset that she’d have to wait that long to get her cable up and going. I apologized many times and told her that she’d need to reschedule a few weeks later, and then I left. Three days later, I was looking over my work orders for the day and I noticed her name and address again.
I thought, “Wow. I bet she thinks that she’s getting a different installer who she can try to convince to give her a different answer.” I was wrong. When I pulled up to the house, I couldn't believe my eyes: She'd completely re-shingled the roof. This lady must have been desperate for some cable. Luckily for her, because of the new roof, I was able to install the satellite dish.
Wikimedia.Commons
92. A Silken Flight
I used to work for a company that modified aircraft for really rich people. I’m talking about 747s, not Gulfstreams. This company had made several aircraft for this one customer, who I was told had purchased a new one solely because his spiritual advisor had told him that one of his current planes was bad luck. He still let his wife use it for her personal travel.
To me, one of the most exquisite features of these planes wasn’t the gold-plated everything or the rare wood veneers, it was the silk carpet. That stuff cost over $1,000 per square foot and felt like walking on a bed of angel feathers harvested in the most inhumane way possible. Granted, these guys didn’t deck out the whole plane, just their personal areas, but yeah…silk carpet.
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93. Game On
I did IT work for a tiny little private company which was basically the owner, his brother, and me. The guy called because his new PC wouldn't turn on. It was about 3 pm and he was fully willing to pay for me to drive 5 hours one way to get it working that day because he wanted to play games that day. So, a 5-hour road trip later and I pull up to this sprawling mansion.
I thought that I was in the wrong place. Still, I used the intercom at the gate and found that this was, in fact, the place. The guy and his wife were really cool and the dude had built his own gaming rig, which was absolutely over the top, I had never even laid eyes on hardware that expensive before. Turns out that he had never even turned the power switch on his PSU on.
He still gladly paid me the base rate of $1400 for me to come out there to flip a switch. I also installed his drivers but that was technically free. And the most mind-boggling part of all? He also gave me $5,000 in cash as a tip all because he was excited to play League of Legends on his new PC.
94. Christmas Spirit
I was invited to a Christmas Dinner by an extremely wealthy Korean family while I lived in Seoul. They were a very nice family but I think, in hindsight, that they wanted to show their friends that they had foreign friends like me. The wife had everything catered and the home professionally decorated. It felt like we were in a department store.
There were multiple Christmas trees, a working train set, staff handing out appetizers on plates, etc. It looked like she had studied Christmas movies from the USA and copied everything. The dinner was served on an absurdly long table with two huge, perfect-looking oven-roasted Turkeys and all of the trimmings. I was later told that Koreans don't like turkey.
These ones were just for decoration and would be thrown out later. We ate Korean food. The family said that I could take a turkey home and that the caterer would drop it off with anything else I wanted.
95. Just Redecorating
I have been working for the super-rich for some time and the craziest thing I've seen was a brand new 90-meter multi-million-pound yacht built in the Netherlands. Its maiden voyage was to Antibes in France. The owner came on board and left after a few hours. The next week we were sent to Genoa, Italy, where all the bathrooms on board were ripped out and upgraded.
I'm talking about brand new marble sinks, showers, floors, and lobbies all crowbarred out. I’m talking about tons of brand-new polished marble just chucked to the wayside. The new marble colors and patterns arrived in the weeks following. There's ‘feed me money,’ there's ‘in your face money,’ and there's ‘it's not even a thought money.’
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96. 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.
97. Feeding Time
I have worked for some of the richest people in Maryland and the one thing that stands out more than others is this doctor I worked for in Montgomery County, one of the most affluent zip codes in America.
This guy owned a lot of offices around the DC area, employing tons of employees and associate doctors, etc. He was really wealthy. He had a place with a huge garage full of exorbitantly expensive cars like Ferraris, an art collection—the works. I used to do IT work for his medical practice and managed all the servers, etc., and occasionally went to their house because I was the lead admin.
Once, I was working in his house and was walking around upstairs where the bedrooms were when I came across the most off-putting sight. What I see is that this guy was lying in bed being fed by an assistant. I mean, he was literally lying in the bed while someone, completely platonically, hand-fed him, and not something like grapes but a regular meal. It was strange, to say the least.
Imagine someone feeding you a full meal with things like a steak and spoons of soup, salad, etc. and you never use your hands. It was like an adult being fed like a baby. I've never seen anything like that before and that was what popped into my mind, like a dictator or something who demands to be treated like a literal king. Keep in mind this was a man in his 50s who was in fine physical shape and didn't need a caregiver. It was just pure opulence.
98. Missing Fairy Godparent
A colleague of mine used to be a bouncer at a club that was the place for rich kids to hang out. He saw a lot of the typical “look at me I’m so rich!” behavior. Things like buying the most expensive champagne in the club and telling the bartender to pour it down the drain, wearing several Rolex watches and handing them out like candy to strangers or tipping the staff thousands of dollars were not uncommon.
The thing that stuck with him the most was just how far removed these kids were from reality. In particular, one disturbing incident stood out to him. One night he had door duty and didn’t let a kid under the influence into the club. So, what did the kid do? He decided that it was a good idea to take a swing at him. It turns out that it wasn’t a good idea.
The kid found this out quickly after he was lying face down on the ground, handcuffed with his hands behind his back. But even now the kid didn’t seem to be too worried, he just kept saying, “It’s all right, just call my dad and he’ll sort this out,” over and over again. He seemed incapable of realizing that he was actually getting busted for attempted assault.
Not even when the authorities finally arrived and put him in the back of their car did he seem to fully grasp the fact that he was actually in trouble and that his dad wouldn’t show up, wave a wand, and make this all go away.
99. Throwing The Baby Out With The Bathwater
I’m a retired paramedic. I've seen a lot of messed up stuff—but one moment was worse than all the rest. I was once told to immediately place a freshly delivered newborn baby back inside of its mother’s body. She delivered in a transport ambulance en route to the Weill Cornell Medical Center. She then lost her mind over the fact that her baby wasn't born in a hospital and, furthermore, not born in a good hospital.
As a result, the mother then told me to "hold the baby in with your freaking hand!" I explained that this wouldn't work and that we were having this child on 3rd Avenue. She completely flipped out and started yelling at me like a complete lunatic. Finally, she and I made an agreement that I would say that the baby was still inside her body until we backed up at the hospital driveway.
I guess this satisfied her requirement of her kid being born at a hospital versus next to a dry cleaner’s on 3rd Avenue. So, as far as that kid knows, she was born in the Weill Cornell Emergency Room Ambulance Bay. She will never have any idea how much turmoil surrounded her birth, and how unreasonable a request I was given in the process.
100. Helicopter Parents Never Fly Coach
I worked as a nanny for a 1% family. The stuff I saw haunts me. I remember having one parent complain how rude it was a friend hadn't offered to fly them to Miami on a private jet for a weekend getaway, and they were "forced" to go first-class. Had the other parent tell me they thought it was really "sweet" I was happy to help others and never be wealthy.
They would also spring last-minute trips on me and their kid all the time, so I'd stay in the main house with their child while the parents were country-hopping. Poor kid never had any sense of who was going to be where. There were business-related videos of the parents on YouTube, so it got to the point where I'd play them on an iPad so the kid had some sense of consistency.
Just to be clear, the kid was absolutely adorable and very sweet (which made it really hard to leave, I felt terrible), but it was pretty disheartening to think they'd probably turn out like their parents in a few years. The best part about the parent complaining over the first-class flight was when they asked me if I thought they were overreacting.
Literally asked me "Wouldn't you be upset? Don't you think that's rude? They've been doing better [financially] now that they have Company X money they could have sent a plane etc." and I'm thinking, well I'm pretty sure my entire year's salary couldn't pay for one chartered flight, so you know I'm probably not the best person to ask.
