Whether it’s making frivolous purchases, demanding outlandish requests, or just really off-putting behavior in general, rich people like to think that they can get away with anything. Thanks to the people of Reddit, we’ve compiled some truly outrageous accounts of the lifestyles of the rich and famous—including the good, bad, and the very, very ugly.
1. A Truly Fancy Feast
I once had a customer who ordered $150 of caviar to go…for their cat.
2. Sliding Scale
I had a guy put a $20 on my host table when I came to greet him and his wife and say, “This is your tip. However, every time you do something wrong, I will remove a dollar.” I thought he was joking, so I chuckled and asked, “Like, what?” He takes the 20 off the table and replaces it with exactly $19. Who carries enough bills to do that? He responds with, “Like that.”
3. Sounds About Right
A kid I know claimed he wasn’t rich by saying, “I don’t get to pilot my helicopter as much anymore.” The guy sitting next to him, when prompted to define an income bracket for the middle-class, couldn’t answer. He eventually arrived at a $700,000 annual income as a rough estimate. For a middle-class salary.
Neil Armstrong’s nephew or grandson or whatever was attending Space Camp the same week I was. There were many rumors of him being a little brat. It was confirmed true that almost every day he was at risk of getting kicked out. The last day of camp Neil actually spoke to a huge crowd of space nerds. Minutes before the speech, that little brat got kicked out, publicly, in front of mostly everyone at the camp. Neil must have been so embarrassed.
5. Non-Consumable Conspicuous Consumption
There’s a thing in Stockholm‘s rich kid district called “vaska.” Basically, you order an expensive bottle of champagne, pay for it, and watch the waiter pouring the bottle’s contents down the drain. Some places even let you do it yourself. Sadly, it’s an established thing in these kinds of circles. Like it’s on the menus and all that. Honestly the dumbest way of flexing I’ve ever witnessed.
6. Don’t Enable Rich Jerks
I worked at a restaurant in the lobby of a rather nice hotel. There was a rich dude that basically lived there. He would eat in our restaurant every night. Our chef had to handpick his steaks from a local butcher. The steaks were massive. It was always specially prepared just for him. Every single time this person would take two or three bites and complain to everyone in earshot that his steak was terrible. Every. Single. Time.
This dude was odd. He would only drink the cheap wine that we served by the glass. However, he would request that you open a fresh bottle just for him. He couldn’t possibly drink a glass of wine out of a bottle that was first opened for someone else. Even if I just opened the wine and poured a glass to the person next to him.
That bottle was considered “tainted” to him. If you are that annoyingly picky, just buy your own darn bottle of wine. Oh, and one last thing. He parked in the handicapped spot out front, even though he was not handicapped. But because he spent so much darn money at the hotel, the managers refused to make him move his car or have it towed.
7. Direct This
Over the summer one year, I signed up to be an extra for a film by a man who had won a fancy award for directing a particular film because I liked theater. When I got there, I actually ran into the director almost immediately, who proceeded to tell me that I would no longer be an extra (even though I said twice ‘No, sir, I’m supposed to be in these three scenes’). Why?
Well, instead I would be his wife’s assistant for the day. She wasn’t in the movie. She was just observing all day. But she still had a change of clothes for when she left that needed to go in a dressing room (again, even though she wasn’t acting in the movie). The guy, from what I can tell, is just the egotistical kind of wealthy, and not actually SUPER rich, but the award went to his head and he used it as an excuse to treat everyone on set like trash.
8. High-Priced Trauma
I worked for a psychiatrist, and we had some VIP clients. One client was the gay lover for a really wealthy old man; he owned one of the major pharmaceutical companies. Apparently, this rich old man took our client for a lover while he was in his 30s and the client was in his very, very early teenage years. Like, we’re talking 13 years old. But that wasn’t the worst part.
The rich guy just buys the kid from the family to be his lover. It was in the late 70s or 80s. Their lifestyle together was sort of like this, “take Private jet to France, rent 5-star hotel penthouse, party like heck for a few days. Take Private jet to Rome, rent penthouse, party like heck for a few days…” you get the drift. I had some other interesting cases too, safe to say same rules don’t apply to the super wealthy as us regular mortals.
9. We all Need to Call out Crummy Behavior
I saw an American woman who seemed to be a model out for breakfast at a nice hotel in Barcelona. She demanded the waiter walk the butter over to her table. It was 4 feet away at the breakfast buffet. I actually stood up, grabbed it, and handed it to her, as she was demanding this in English to the Catalonian staff. She actually said, “No, I want them to do it.” I said she was an embarrassment, to which she stormed out. Doing my part!
10. Proxy Parenting
He wasn’t super rich and powerful, but I used to work for a pretty reputable set of attorneys a few years ago. I started off file clerk and went up to receptionist. Anyways, one of the attorneys specifically just did not got a darn about his kids whatsoever. He didn’t know their ages or their birthdays. He would have the office manager mark down all these things on her own personal calendar so that she could prepare gifts and whatnot for their birthdays.
He even had her paying all their bills and rents (some were in college) with his checks. One of his stepdaughters worked there for many years and he would sometimes forget about her and leave her in the office alone. She would have to call just to get picked up. The attorney was a pretty crummy guy but his complete lack of interest or care in his children’s lives always disturbed me.
11. I Only Love My Bed…I’m Sorry
I work at a luxury property in California and we once had the co-founder of a large payment processing company stay with us. He only liked to sleep on his own bed, so when he woke up that morning, he paid a team to load his bed into a truck and have it delivered to our property. We then removed the bed in his luxury suite and set up his bed that his team had brought us. He only stayed with us one night and the process was done to send the bed back home the following day. It kind of blew my mind that he went through all that trouble, just so he could always sleep on his own bed. To each their own, I guess!
12. Whining About Wine Prices
My son-in-law was working as a waiter in a fancy restaurant in Dubai. A very tipsy customer ordered a bottle of a 1960 Pomerol Bordeaux valued at $15,000. He was trying to impress his lady friend. My son-in-law confirmed the price with him and asked him if he’s sure that he wants to open their most expensive wine in the house. He replied yes. The following day when the customer sobered up phoned in to say he made a mistake and wanted his money back. Naturally, it was too late for the restaurant to do anything. They also found out that his lady friend was, in fact, a call girl.
13. Why Are People So Terrible?
When I was a waiter, I once had a woman and her friends at one of my tables. The woman asked for a can of Coca-Cola. When I brought their drinks and gave the woman her Coke, she looked at me, and, in that typical rich person voice, said “Excuse me, honey? I asked for Fanta, not Coke.” So I apologized, wrote it onto my notepad, and went back to get her a can of Fanta.
Brought it to her, and 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 went back and got her a Cream Soda anyway. And surely, when I returned to her table, she did the same thing again, “I asked for Sprite. Should I call the manager?”
So, for the last time, I smiled and I went back to the kitchen and packed one can of each: 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 darn Sprite out of the plastic box and said, “Just leave it.” Her friends were silent throughout the whole ordeal and none of them gave me any issues further on. I didn’t receive a tip, as expected, but I shrugged it off.
14. Making Amends
A girl at my high school constantly whined and complained because her parents refused to move out of the master suite of their mansion. She felt that she deserved it, because the attached walk-in closet and bathroom were bigger than hers. To reconcile this, she had her parents pay to redecorate her room every single year.
15. Side Gigs
Leader of company, that’s a subsidiary of another company, puts pressure on employees to work on his own side business that’s not affiliated with the company. Basically, he’s ripping off the parent company.
16. Some People Are Not Totally Corrupted by Money
One of my best friend’s fathers is very successful in the tech industry and she has what we call “the magic credit card.” Her dad’s financial manager pays the bill, and who knows if there’s a limit. They weren’t always this rich, and she really is a down to earth person who doesn’t spend extravagantly except when it comes to traveling or eating at fancy restaurants.
When I visit her, she often likes to take me to the nicest restaurants in whatever city she lives in. She likes to order almost everything on the menu because she can’t decide what she wants, including all the cocktails. Sometimes for the more expensive items or things that are priced by weight, the staff remind us of the cost to make sure we can pay.
She usually (sincerely) says, “Wow that is kind of expensive… but let’s treat ourselves!” The kicker is at the end when we obviously have all this food we can’t finish she asks for boxes to take it home. They usually try to tell her that it won’t taste as good reheated, but she just tells them that it was so good the first time and she knows she will love it again. She’s very sweet and a huge tipper, but it cracks me up because I know people are thinking what is up with this chick.
17. Spoiled and I Know It
I have a billionaire customer with four kids, and all of them are pretty spoiled. However, the worst case is the youngest one, who once said to me spitefully “We’re going on Tiger next week and you’re not allowed to come!” Tiger is the name of their yacht in southern Italy. It’s not just that he’s spoiled that gets to me, it’s the fact he knows it and rubs it in purposely.
18. Where Did the Dollar Go?
I used to work at a luxury car dealership as a mechanic. When the market tanked in ’07-’08 we were all convinced to take a dollar per hour pay reduction. That year…THAT YEAR the owner bought a Maserati and we all got watches for Christmas for hitting some goal.
19. Later Years Steinbrenner Was Never Afraid to Spend
I was at a restaurant in Houston in 2004 during the MLB All-Star Week. Yankees owner George Steinbrenner rented out a large area of the restaurant and brought players, coaches, and staff to eat brunch. We got there and were seated as all the MLB folks were leaving. I’m a huge baseball nut, so seeing all of the players was really cool.
Anyhow, our waiter came to our table to welcome us and get our drink orders, and just had the happiest look on his face. I said, “Man, must be cool to be on schedule when these guys come in.” He proceeded to tell us that he and his wife were the two servers for the baseball group, and that Mr. Steinbrenner left them a $50k tip. I’m not a Yankee fan, but looked at Mr. Steinbrenner a little differently from then on.
20. Rich and Judgmental—A Terrible Mix
During our honeymoon, my husband and I came back to our very nice hotel from a day full of hiking looking like homeless people. We were waiting for the elevator with another couple who were both giving us the side eye. Once on the elevator, the couple pressed the button for the top floor, which was the same as ours.
After about 30 seconds of silence and glares, the woman turns to me and condescendingly says, “You need to press the button for your floor.” I told her our floor was already selected and she had the audacity to ask, “You have a suite on the top floor!?”
21. Typical Karen
When I was a server I would always record my tables’ orders. Even though my memory is good, my handwriting is bad so I didn’t want to take the risk of getting something wrong. My manager said it was ok and he even put a sign up stating that some of the staff may record your order for accuracy purposes. Seems normal, right?
At the beginning, I ask each person for their name before I take any drinks or food orders. One of the people at the table orders a steak well done, which is gross but whatever. Food comes and she said her steak was not medium rare like she wanted and I apologized and told her that she did order it well done. Here we go…
This sparked a big rant, lots of cussing, a call for the manager, etc. Again, I apologize and say let’s go to the tape. The look on her face when I played back the recording of “And Karen how would you like your steak?” was priceless. She tried to play off that it wasn’t her but nobody else ordered a steak at her table. Her friends just laughed at her.
22. A Step in the Wrong Direction
I went to high school with the son of the owner of a large TV company. He thought he should be allowed to sit alone in the classroom surrounded by unfilled desks. I had the “privilege” of sitting in front of him and was constantly harassed with attacks from his ruler and pens if he thought I was even remotely leaning back.
23. Rich People Can Buy Things You Didn’t Even Know Were for Sale
I worked at a 5-star hotel. A pretty normal looking guy came in one day and inquired about the price of a piece of art on our wall. It cost $200, 000 and he bought it on the spot, all within 20 minutes.
24. Always a Bonus When Your Manager Has Your Back
My wife used to work at a high-end clothing store in Manhattan—the kind with really expensive pieces of clothing you had to make an appointment to just see. She said 90% of people there would return all kinds of clothes. Saying rich people are the cheapest or would get it just for show. One guy got in a huge argument and rudely called her fat, because she wouldn’t accept 6-month-old satin socks that he wanted to return. My wife was clearly pregnant at the time, the manager was a sassy dude that wouldn’t tolerate that and cursed him out into the street.
25. Aunt Covert Burn
My rich aunt doesn’t let us park in front of her house because it makes her mansion look bad.
26. All That for a Table?
The one story that comes to mind was when I had this awful encounter with this guest who didn’t have a reservation and wanted the best seat in the house, which was already reserved for another guest, a regular who was coming within the hour. She was probably in her 80s, smelled wealthy, and was drenched in diamonds.
She pointed her crooked finger to the table in the corner and said, “I want to be seated there now.” I apologized and offered her another table that was just as desirable to my VIPs. She slammed her hand on the podium and croaked, “I dine here all of the time—I live here on the island! I know the chef and that table isn’t taken, so I will sit there!”
My years working in fine dining taught me that I had to be confident, assertive, yet gracious. If the clientele sniffed weakness from you, then you were done for. So I explained to the guest that the person who reserved the table, reserved more than two weeks prior and that perhaps next time she visits, she can reserve that table, and in the meantime, I had a number of exclusive tables for her to choose from.
I knew she was lying about being a regular, and many clones of her say they know the owner just to save face in front of their elite friends. So I wasn’t impressionable at that point. But when I told her that, she responded by glaring at me and sneering “You’re treating me like a black woman!” Fuming, I uttered, “Excuse me?” Before I totally lost it, my manager came to the rescue. I had to go to the break room and regroup from her audacity—all over a table! Palm Beach is something else.
27. Car Trouble
On my friend’s 16th birthday, her step-dad gave her his one-year-old hummer. She full on cried when he tried to give her the keys, because it was both used and “the wrong color.” Naturally, they went out and bought her a brand new one in the color she liked that same day.
28. The Nanny Dairies
I’m a nanny for a rich family. When I get paid (in cash) my boss says, “Man now I’m gonna have to go all the way to the bank to get more cash.” Not wanting to go to the bank isn’t the annoying rich thing. It was an annoying rich thing because he had $500 still in his wallet, and he was complaining it wasn’t enough money to have in his wallet. But wait, there’s more.
Also, when they travel they prefer two-bedroom suites, one time they could only get a one bedroom and he said, “well that just ruins the whole trip. Finally, My car got broken into and I mentioned it felt so awful to drive it knowing someone was in it. His idea of empathizing? “That happened to me. I HAD to buy a new one.”
29. Rich People Quirks
I worked as a busboy at a restaurant in a hotel that was at the end of its life. The owner, a reputed mob boss, and his eccentric wife lived in a top floor suite that was two stories tall and lined with white marble, Italian statues, a red carpet, etc. The wife would do her grocery shopping from the restaurant’s kitchen, and it would be us busboys who took it up.
However, she made very specific demands on how the food should be prepared. Once, she asked for seven pieces of American cheese, and it needed to be on a plate in a star pattern. Another time, she wanted five raw eggs, each wrapped in a napkin and then wrapped in plastic, placed inside a large Styrofoam cup. Failure to prepare the food to her exact specifications meant being fired.
On top of all that, she never once met us when we brought the food—she would buzz us in and instruct us to put the tray in their private elevator, and send it up to her. I was once berated because I put a plate of bread on the left side of a tray instead of the right. After the husband died, they closed the hotel. For a couple years after, she lived in that penthouse alone, and it was creepy to drive past at nights and see this 14-story hotel completely dark except for her couple lights on the top floor.
30. One Man’s Castle Is Another Assistant’s Prison
I’m a personal assistant for a doctor. He asked me to clean his apartment which is one of the nicest places in town. As he’s showing me through all the doors to actually get to the apartment (place is like a fortress), he slams each and every one in my face.
31. The “Fun” in Family Funds
A cousin of mine is on his third Porsche 911 after he wrecked the first two. He told me that his parents said if he destroyed it again, they’d just buy him some other car. He wrecked the first one while drunk, and thankfully, he somehow didn’t injure anyone. I don’t even think he got charged with a DUI. But that’s just my cousin: there’s also my horrible family.
My family usually charters our own plane whenever we go on vacation. It costs something like $6,000 per hour or something. One year the company overcharged my dad for a miniscule amount, I think it was like a grand. And he was considering disputing the charge or something, ignoring the fact that $1,000 is nothing to us, and he already paid $36 thousand for a flight. Oh, and my parents hate tipping the pizza guy for some reason. They have no problem tipping a waiter 50% or even 100% at a fancy restaurant, but the pizza delivery man? Nope.
32. Museum of Woe
Old Masters oil paintings, and modernist masterpieces—recognizable ones you studied in school—leaning up against the wall, stacked against each other. Also, the wife’s $40,000 per place setting china from which she ate her boxed Mac & Cheese. I should add that there were a dozen or more of these museum-quality paintings strewn carelessly about the nondescript den of their freaking beach house—with windows open to the sand and corrosive salt air.
33. We Can Afford to Try Them All
I used to work as a private chef for a billionaire, living in Paris. He is actually a very nice and down to earth guy, treated everybody very well and was just a normal guy that had a lot of money. One time we were at his private villa in southern France with three of his (also very rich) buddies. Let me tell you: rich people are not just like us.
They flew in by helicopter some 10-12 smoking hot Russian models that stayed at the house and partied for five days. Lots of partying with good and expensive food and drinks, etc. At the end of the week, he had slept with every one of the Russian girls. I’ve worked for a lot of really rich of people and would say that this is nothing unusual.
34. You Can’t Put a Price on Leg Room
I was an assistant to a rich guy who routinely had me buy two first class plane tickets, so nobody could sit next to him on the flight.
35. As High as the Money Stacks
I was a concierge. I seen lots of things, but the one that made me the most mad was two very well-off families in the building (lawyers and consultants…they were neighbors and best friends). Extremely conservative and active in trying to deny any kind of social services in the city and state. 4 pm was “cocktail hour,” as they called it.
They would load up on all sorts of prescriptions and sit in the lobby bragging about how high they were. They had no shame about hiding it. Sometimes if the husband/lawyer was really far gone he would loudly discuss his clients’ cases in front of everyone. Then their prep school kids would arrive home and everyone would head out to the most expensive restaurant in the neighborhood. Other than that there was a lot of general entitlement, shacking up with people who aren’t their spouses in the building’s swimming pool, etc.
36. Personal Piggy Bank
The director of my former company was a nice enough woman, but she used her position to get employees to do everything for her. The head of Human Resources & Finance was required to help manage her personal bank accounts, enrol her children in school, book her holidays, EVERYTHING. She also had a nanny for her younger kids who was somehow being paid through the company for tax purposes (and so she wouldn’t have to outlay the money).
37. The Price of Love
My neighbor is this really down-to-earth guy who managed to work his way from nothing to being quite wealthy (he has his own company and pulls in north of $200,000 USD per year). A few years ago, he married this beautiful brunette who can safely be said to be on the upper scale of maintenance cost. Worse than that, she was given way too much freedom.
When they redecorated their mansion, they ordered custom-made stairs that cost about $100,000 USD, which were made of glass/steel. Once she had them installed though, she noticed that they didn’t really match her choice in furniture, so she had a virtually identical set of stairs made that only differed from the last set by a few shades of white. How this guy puts up with her is beyond me.
38. Dishing It out
Someone once ordered the dessert on special—it was tiramisu that day—and sent it back, saying that “Mascarpone cream doesn’t go along well with coffee and your recipe should be changed.” That is literally the original and classic recipe. Then get this. She asked for tiramisu with Victoria sponge. Are you kidding me?
First, we had no Victoria sponge, second, just because someone asks for it we are not going to make something we won’t end up selling, and third, I think the chef would’ve rather carved his own eyes out with a fork. Just because you have the money to pay for a 200€ meal doesn’t mean you are entitled to whatever you want. We are workers who want to turn a profit at the end of the darn day, not your personal staff of cooks and waiters.
39. Time Is Money, or So They Say…
I work for a very wealthy family in the commercial real estate market, and the one thing I have noticed is how much they lack a sense of time. They have had people doing everything for them for so long they no longer realize how long it takes to complete a task. One example: “Hey take this deposit to Bank A it HAS to be deposited today!” Sir, it’s 4:50, they close at 5:00, and it is a 25-minute trip one way.
40. Nay Is For Horses (Which I Own)
My dad is a self-made millionaire. He accomplished it through hard work, and he raised me just as toughly as he was (he didn’t want me to depend on money). I have some experience with people of my “status.” One girl I know convinced her parents to move so she could be closer to the horse stables she liked to ride at.
She upped her dad’s drive to work, and her mom’s, and her little brother had to change schools in eighth grade, the worst time to pull a kid out. Get this though, she made her mom BUY her favorite horse. She also would try and make ME buy her a horse, because “I was rich, and I didn’t need my money like she did.”
41. You Probably Know What Evian Is Spelled Backwards
I worked at a private villa in Bali. One guest stood out because she only drank and bathed in Evian. So one day I spent almost an hour filling a large tub with tons of Evian bottles. The same young woman complained that the path from her villa gate to her room wasn’t well lit. This was probably because she wore sunglasses at night.
42. Outbid by the Law
I had a pro golfer hire me solely to list 90% of his belongings on eBay. Everything from huge TVs to golf club head covers. The odd part was he wanted EVERYTHING listed for $0.99 and shipped as fast as possible when it inevitably sold. I lost that job when he went to jail for procuring said items with illegally gained funds from his invalid sister’s inheritance.
I was questioned, but since I had no idea how he got rich, no charges were ever brought up on me. I just thought he was a weird eccentric rich guy who wanted new toys, and I assumed he had invested his pro-golf earnings over the years (he was sponsored by Nike after all).
43. Poor in Practice
I worked for a non-profit that helped extremely low-income women start their own businesses. These women would give up food to scrape together enough money to join our program. One of our E.D.s said she “wished she could relate to our clients more, but she has never been poor.” She owned two homes in one of the most expensive zip codes in the US. Also, another woman, whom I really did respect but didn’t always agree with, believed people chose to be in poverty. We would debate for days about that statement.
44. Hey, Big Spender
This one girl only ever wore designer clothes and would constantly make fun of people who couldn’t afford to wear the same. When we went to the mall, I would often buy nothing. Meanwhile, her parents would give her not one, but two credit cards to go buy whatever she wanted.
45. A True Diamond in the Rough
I operated a premium chain restaurant in Canada. One day, a very generous gentleman we’ll call Mr. S started coming in. On the first day, he spent $200 on wine and tipped $1,000. The next day he did the same. When he came in for the third time, I had servers fighting over him. Anyway, one evening he got drunk on wine and Brad the busboy made the mistake of complimenting him on his watch. Mr. S. takes off his Tag Heuer and gives it to Brad.
The next morning, Mr. S comes back to get his car and asks if Brad is there. I say yes and go get him. Brad knows what’s up and is removing the watch as he walks over to Mr. S. Mr. S then says, “Brad I’m really sorry I got drunk last night and gave you my watch.” Brad is chuckling as he is removing the watch and says it’s no problem, and he was just holding the watch until Mr. S returned. But he was dead wrong.
The next thing Mr. S. said, I could not believe: “Brad, you don’t understand, I’m sorry because it was very rude of me to give you a used gift.” And at that moment Mr. S pulled out a box with a brand new Tag Heuer inside and handed it to Brad.
46. Poor as Porsche
The CTO of an IT company I worked for was born into a rich family and didn’t know how to talk with his “inferiors.” He was so bad at human interaction, our CEO forced him to go to some kind of class to learn how to interact with humans. This douchebag loved Porsches. He drove a couple to work, and he had one he would race at amateur races occasionally. But that wasn’t the worst of it.
One day, one our coworkers failed to meet us for lunch because he was broadsided on the way to the restaurant. For some reason, after the accident he came back to work. We were standing around his cube and he’s telling us about his car getting totaled when the CTO walked up. After hearing the story, the CTO says (and I’m not embellishing) “At least it wasn’t a Porsche.” Then he laughed and walked off.
47. Disrespecting Your Elders
This one girl whose mother I used to know would spit in her Granny’s face if she didn’t give her money every time she saw her. She also told her dementia-ridden Grandpa that she couldn’t wait for him to die so she could buy herself gifts with the inheritance money.
48. Was His Boss a Bull?
My former boss was insanely wealthy. He used to stay in presidential suites at hotels and would order the staff to have any and all red removed. He was a high roller at several casinos and they made special chips just for him, as a substitute to red chips. He hated the color red because when you’re losing money, you’re “in the red.”
49. She Doesn’t Sound That Nice…
I was good friends (and still am) with this kid whose mother was an executive for a big gaming company. Basically, she would attend Pax East (pretty big gaming convention) every year and would give her kids tickets for themselves and their friends. I wasn’t one of those friends that year, but I got tickets for Christmas and we still went together and oh my god, what his mother did literally sent shivers down my spine.
We went to the booth where she was at (that year she was advertising a new game, I don’t think it ever hit off, if it did I don’t remember the name of the game then). When she saw me and her son get to the little show floor, she pushed every kid out of the way so that we could be first in line, and actually got a kid kicked out for throwing a fuss about it.
I wanted to say something, but my parents had paid $50 for me to get to the convention and I wasn’t looking to get kicked out before even being there for an hour. She was a nice lady though, she was able to get basically a few of everything that the popular exhibits were handing out (hats, shirts, wristbands, coupon codes).
50. Aren’t They Precious
Young girl about five years of age, getting ready to go into New York City to visit her Grandmother. She was at her Aunt’s house and did not have a pair of shoes that she liked. She called her chauffeur, told him which pair of shoes she wanted—the dude got the shoes and drove some 20 miles to deliver them, and she told him he got the wrong ones and he was an idiot. No one in the family thought this was inappropriate.
51. Not a Slice to Be Spared
I worked for owners (three brothers) of a private bank and managed their properties. One had first edition uncut classic books purely for decoration. He also had a Rolls Royce, which required new tires due to sitting unused for months at a time—the steel belts flattened from the weight of the car. Oh, but the women of the family were even worse.
One wife called me all but accusing someone (me?) of eating an $8 pizza at their country club, which after numerous far-more-than-$8 international calls turned out to be her son in town having lunch. This from someone with a running balance over $10m on any given day.
52. Power Trippin’ at a Suburban Marriott
I work at a Marriott, one that is more expensive than your typical hotel, but by no means a place that millionaires or celebrities would come to, especially because of our suburban location. However, that doesn’t mean I don’t often get people who think that because they are paying $150 a night on a Marriott hotel room—honestly not that much but it feels a lot to them—that they can be just as rude and entitled as a patron of a swanky upscale hotel.
My favorite little story is the guy who was shooting hoops at our sports court way too early in the morning. When I asked him to stop, he just looked at me and threw the ball as far as he could into the parking lot, saying, “I’m paying too much to be treated this way. I’m talking to your manager.”
53. And Party Every Day
My ex had this friend whose parents were loaded. He lived in an upscale apartment downtown with just him and his girlfriend. Didn’t have a job. Dad paid for everything. All he ever did was throw parties and go to music festivals, even ones out of the country. Didn’t know the meaning of a dollar and always threw fits if any little thing didn’t go his way.
54. Why Leave Your House at This Point?
I know a lady who has one of the lifetime first-class passes on American. She has a house in Hawaii and wanted to fly to a city on the mainland, but she doesn’t like first class from Hawaii because she had a bad experience one time. So, no problem, she can use her NetJets private jet. But she doesn’t want to pay for it. So….
She arranged to make another large donation to her alma mater (she already donated between $10-20 million), and so she calls the president of the university, makes the arrangements, and suggests that they give an event for this donation. Just so happens, a decent number of other wealthy alumni live in Hawaii, so why don’t they all fly over for the event on a larger private jet, and oh by the way, the university should cover the cost of the charter.
55. When You’re Rich, the World Is Your Toilet
I was once a server at a high-end steakhouse in Newport Beach, California. A rich guy’s son comes in, probably in his mid-30s, with a big group. They get a private room and spend thousands on food and booze. The guy gets hammered and instead of climbing the stairs to take a leak, he just relieves himself in the hallway. On the floor. He didn’t get kicked out, either. They just had a janitor come in and clean it up and the dinner kept going. Nice to have that kind of money, I guess.
56. Bank of Dad
I occasionally hung out with a kid whose dad was super rich. He would just ask for money and get it. He tried to use an ATM and had no idea how to, so he asked me or someone else to get money for him. It was so confusing for him. Most simple tasks were incredibly difficult because he was raised not to lift a finger.
57. You Worked for Gob Bluth?
I became friends with a colleague, a delightfully wealthy man and a minor member of European royalty. He wore bespoke suits on his time off, like, he specifically had them made for lounging. He had a £12,000 walking suit. He was very kind and affable, however out of touch with reality he was. I taught him how to order pints at the pub. The first time I showed him how to do it, he didn’t have money because he never carried a wallet. He was in his 40s and led an active social life, but always had a servant on hand to do everything.
58. You Can’t Always Get What You Want
I work retail at an electronics store, and it was launch day for a new product. A guy and his 13-year-old son came in and asked if we had the biggest and baddest model in a certain color in stock. I told them we had that model in a different color. The father gets a phone call and tells his kid to talk to me. The kid pulls out a wallet full of credit cards and snidely asks, “How much would it take to get me that phone?”
I told him I couldn’t sell him something we didn’t have, but that he could order it online. The father comes back and the kid tells him the news. The father looks at the kid and says, “I have to go to a meeting, I’ll have the driver come get you. Don’t back down.” And walks away. I look at the kid. Challenge freakin’ accepted.
He says, “I read on Mac Rumors that you hold 4% of your inventory for DOA phones out of the box. I want one of those phones.” To which I replied, “We don’t have any for that model because we didn’t get any actual stock for it in.” Long story short, the kid starts screaming in the middle of the jam-packed store.
My team leader, who happens to be there, comes out and the kid tells her that I called him a snobby little jerk. She looks at me like he was a crazy person and somehow convinces the kid to buy a different color. As it turns out, we couldn’t sell him the phone because the cardholder wasn’t present to show ID. I was mad about the whole thing at first, but felt that he got what he deserved.
59. Sharing Is for Suckers
In high school, a classmate of mine turned 16. For her birthday, her parents gave her a brand new BMW—but with the understanding that their live-in maid would get to use it once or twice a week to get groceries and run errands for the family. Unacceptable! A week after her epic tantrum, she received a brand new Land Rover.
60. Money Can’t Buy a Stable Home
I nannied for a tech millionaire. His wife had a raging eating disorder, which she covered up by being an athlete, and he didn’t care enough to address it. They had three children that she couldn’t stand. She had a full-time housekeeper and two nannies to keep her kids from interacting with her. When dad was around, all smiles, as soon as he wasn’t, she would get as far away from the kids as possible. Oh, but there’s more.
She also signed them up for loads of activities so that she never had to see them. They all were in therapy at very, very young ages. I nannied for a couple of other families like this. Wives don’t work but don’t interact with their kids either. They just shop and lounge all day. And there’s domestic violence in these families that’s super well hidden. I don’t like to remember this, but…
I saw a husband inches from his wife’s face, shouting his head off because they were out of post-it notes, and me and the other nanny just kept right on cleaning because we needed the job. Ugh. I hate rich people. They have the kind of problems that money doesn’t fix. There are good rich people, I’m sure. I’ll let you know when I meet some.
61. The Windblown Wingman
I used to be the assistant of a celebrity photographer in NYC. Mostly hip-hop celebrities and New York nightlife. This guy slept with so many women behind his wife’s back, it was obscene. Once there was this model who needed portraits taken, but my boss was sleeping with her and his wife was suspicious. So what did he do? He had me take the pictures instead. Except he drove me there with his wife but had to drop me off across town, so his wife wouldn’t know where I was going.
That’s right, I had to walk 20 blocks to get to the model’s apartment. Also, if we worked until 3am, which was common, I would have to crash at his place or else I would have to sit in Penn Station for hours until the first NJ transit train. He made me sleep on the floor; even though he had a couch, I had to sleep on the floor. Everyone involved in the NYC upper class are horrible people just waiting to screw you over.
62. When the Rich Do Good
I’m a soldier. We held an annual ball for people in the service in our region at a local marina hotel restaurant/bar. We had the whole place reserved for the evening. The barkeep/host grabs our commander a few hours into the event and says, “There’s a guy, he’s a daily regular for the past 15 years and he wants to grab his usual nightcap. Do you mind?”
The commander agrees and the gentleman comes in, sits at his spot, and proceeds to enjoy the show while “occasionally” covering costs for those of us grabbing drinks, in exchange for a little small talk about what we do. After about three hours, he grabs his coat and heads out. He then returns about an hour later and proceeds to shut down the joint with us, still covering drinks here and there.
The next day when I came in as part of the clean-up crew (grabbing drunkenly abandoned uniforms or materials), the host gave me the breakdown after I asked how long their charges normally take to process, as I hadn’t seen my bar tab hit my account yet. It turns out the regular owned a chunk of the marina, and covered a combined $12,000 bar tab as “Thanks to the servicemen and women.” I had a tab of over $450 waiting on my card and it was completely covered. It was glorious.
63. Surprised the Spoon Was Even Taken out of the Baby’s Mouth
I don’t even work at that nice of a restaurant, but last month I got chewed out over the phone because some lady left her baby’s actual silver spoon on the table. We didn’t know where it was, so it must have been long gone.
64. Mat About You
I went on an amazing trip (southern USA) with my girlfriend at the time during the summer and she had an uncle who was very rich, and she was used to all his wealth. I was not. I couldn’t believe that we got to do all the amazing things we did. Money was just not an object or something you had to worry about.
The third day of the trip, I was getting aboard his yacht (he owned the largest one in the club) and it was incredible, glass stairs, stone walls and dark beautiful wood. We all sat down near the back at a table and the wife FREAKED out. She yelled, “Where are the mats?!” Apparently, there were supposed to be “mats” to be set down on the table before the giant glass bowl of chips and freshly made guacamole could be placed in front of us.
She was really mad and almost embarrassed. I’ve never been so weirded out by someone’s anger. I couldn’t believe that it was SUCH a problem. I said to myself, “It’s fine, seriously I could walk in there and grab them in .4 seconds…” I’ll never forget, and I learned that extremely rich people don’t have the same kind of problems that regular people do.
65. Bravo to Having Your Workers’ Backs
I worked in a five-star hotel for a number of years. One wealthy guest was throwing a fit, claiming a maid had stolen a diamond earring. The owner and entire management team told the guest that the maid had not stolen anything and they were sure she’d find it when she packed to leave. Her room was a mess of strewn clothing. Sure enough, she found it when she packed to leave, but she did not offer the maid her deserved apology. Always admired how management from the top down had the maid’s back and never thought for a minute she’d done anything wrong.
66. Generally Awful
So, I will delve into the realm of public knowledge of what happened while I was working for a couple generals. I was a “Driver,” which basically meant that I was responsible for a whole host of things besides actually driving them, from getting them food three times per day, making sure their personal quarters were clean while deployed, laundry, dry cleaning, and making sure that their uniforms were properly put together.
One of the Generals that I had the “pleasure” of working with was a terrible person. He had a long running affair with a subordinate female officer that became very public. During the course of this affair, she persuaded him to fire people for no reason, he used government money for travel to see her, she would write emails from his account to accomplish her bidding, and so much more. He even used his rank to coerce female subordinates to send him nude photos.
67. Rich and Wasteful
I once had to accompany a few rich tourists for a day. We went to an expensive restaurant, they ordered every single dish on the menu. With the six of them, it was around 15 full meals. They took some bites of the food and left. Maybe 20% of the food was eaten. I felt very embarrassed.
68. The “Happiest” Place on Earth
When I was in high school, my family was pretty poor, and I had a fairly rich friend. My single dad spent years saving up for us to go to Disneyland. We finally went when I was 16. Fast forward a year, my friend is going to Disneyland for Halloween break. Her dad told her to invite two friends. So, she invited me and another girl.
I was freaking stoked. But she kept saying, “I don’t know, it’s probably going to be boring, my grandma takes me to Disneyland like every break.” And when we got there, all she wanted to do was sit on benches and text. All of the rides were “boring” and she’d already been on them dozens of times. It ended up being pretty boring for me because I didn’t want to go on the rides without her.
69. Room Disservice
A girl I went to high school with had her own private living room in her house with a flat screen TV, multiple gaming systems, a desktop, massage chairs, and a pool table. Again, this was a bonus room just for her—on top of her bedroom and the rest of the family’s main living room. If her parents ever tried to go in it, she would scream at them until they left.
70. The Devil Tries Her Best
CEO boss lady was built like a linebacker. I’m 115 lbs wet, and small. Her demeanor is like the boss in Devil Wears Prada without any of the earned respect in the industry to somewhat justify her behavior. When I had a stress-related seizure in the office, she climbed on top of me and shoved a stapler in my mouth so I wouldn’t bite my tongue. She didn’t even get off when a nurse told her she was making it worse. Had to be pulled off by fire and EMS. I mean she cared, right?
71. Row Row Row Your Boat
A girl at my high school used to complain that her boat was a foot short of being a yacht. Not her family’s boat. They had a different boat. This was her boat.
72. Wag the Tail
I held the corgis while she gave them each a suppository. Posting before I read the comments, but guessing this rates no more than a 3/10 on the messed-up scale.
73. You’re Never Too Old!
This 30-year-old guy I know named Matt is the most spoiled person, adult or child, that I’ve ever seen in my life, hands down. He abuses substances and still lives at home. His parents literally drive him to the city on a regular basis and give him money to buy junk with. He works at his parents’ restaurant, delivering pizzas in his dad’s BMW. And it gets worse.
He can goof off on the job and take days off all the time, never having to worry about being fired. And the jerk still has the nerve to whine about how awful his dad is! One time, I watched him literally cry his eyes out on the phone, begging his dad for money. As soon as he hung up, he whined because the dad was going through a slow period at the shop and said he would not be able to deliver any money that day. Naturally, this guy ended up landing himself in jail recently—and he may even still be there for all I know.
74. Worktime Is Playtime
My first job was being an assistant to the CEO of a small warehouse-based wholesaler operated as a pet project of a very rich man. The owner had a five-year-old toddler at the time, and calling the kid spoiled would be like referring to the Pacific Ocean as “moderately damp.” This was one of those situations where it was crystal clear the kid had never, ever been told “no” to anything or had any sort of discipline.
For some inexplicable reason, the owner would bring him to work almost every day and let him run free. As the warehouse and accompanying offices were one large interconnected building, this often meant there’d be this toddler running around breaking things, unpacking boxes, and generally making the entire warehouse staff’s jobs a ton more harrowing than they should’ve been, as it was quite clear that making the kid angry in any way would result in the culprit losing their job. This did happen at least once during my time there.
75. Holding Those in High Positions of Power Accountable
I work at the country club where Reince Priebus goes. Every Friday night is “Pasta Night,” where you pay $5-$10 or so to go to the pasta bar where a chef will make you a pasta dish to order. Priebus, upon getting the bill, turned to the server—a girl who was being perfectly polite to him—and demanded to know why he was charged for three adult meals.
He was there with his wife and kid, and the kid was 12 years old. 12 is the cut-off for getting the $5 kid’s pasta, so the server had charged him the $10 for an adult pasta dish. He insisted his kid was 11, so the server apologized and went to the server station in the back where there’s a computer that would let her change the bill.
I and a couple other staff members were standing back there, giving her questioning looks as we’d seen Priebus look angry and gesture to his kid. Had she screwed up the kid’s order or something? She relayed the whole story so far to us and then turned to the computer. Curious, she looked up the Priebus family’s record.
The kid was 12 years old. Still is, probably, as this was only last July if I recall correctly. The server’s older sister pointed out that the server had every right to charge Priebus for a $10 adult meal, and Priebus was the most highly paid White House staff member of all time before getting fired, and could definitely pay the $5 difference.
A determined look is set in the server’s eyes, and she goes out and tells Priebus she knows his kid is 12, to which he responds (and this is a direct quote), “Oh, so that’s how it’s gonna be?” He paid the bill in a huff, didn’t tip her, and left. To be clear: The man who was the most highly paid member of the White House staff of all time tried to lie about his kid’s age in order to save $5 at a country club where most entrees will run you about $25-30.
76. Parting Gifts in the Porcelain
I had a short-term IT contract gig at an investment firm of some kind, (small business, HUGE money), don’t think anyone there wasn’t some three letter job title millionaire. Got to observe some bizarre stuff. Most of the offices (for the upper-ups…. Actually they all seemed to be “upper-ups”) had private bathroom.
If someone was out for a meeting or whatever offsite, multiple people would intentionally take the nastiest dumps in that person’s private bathroom, and not like one person, like six or seven in series performing some kind of pre-planned unholy train of war, stench, and destruction. Seriously, they timed this. Giggling like a bunch of prep-school teenagers in suits that cost more than my paycheck.
And the messed-up part, it was like a routine thing around there! Everyone was doing it to everyone else. Guy would come back, find his private throne closet reeking of death and colonic waste demons hanging thick enough in the air to distort visible light, and be laughing their butts off “LOL! Oh you guys got me! Har har! Got em good this time.”
What made it more unsettling was there seemed to be a kind of etiquette system built in to the activity too, apparently if someone was actually mad at you, they’d skip flushing, or run hot water to add “extra steam,” AND half the time the victim could accurately name the last person who’d attacked the bathroom.
77. Listen to the Grocery Store Clerks
I worked at a grocery store in uppity Gold Coast Chicago when I was a teen. We sold soup for lunch and when bagging them, we put it in a paper bag followed by a plastic bag to make sure it was secure. This one time, a woman came in to buy soup. I proceed to bag the soup and she says no, “I’ll just put it in my bag.”
I ask her, “Ma’am are you sure?” After all, her bag was a Louis Vuitton bag that looked brand spanking new. However, she insisted that she didn’t need the extra protection. Of course, 15 minutes later she comes in raging that she has minestrone juice all over her Louis Vuitton and demands to speak to a manager.
I was once friends with a Chinese girl whose family net worth appeared to be in the hundreds of millions of dollars. She told me a story about her rich uncle who owned a super yacht and loved to travel around the world. Apparently, his favorite thing to do was pull up into a port and bathe in the stares of everyone admiring his yacht, since it was always the biggest one.
Well, one day he goes somewhere, say the Bahamas, and he pulls into the port and he isn’t getting the usual attention since someone else happened to have a bigger yacht than him for once. This girl said it ruined his whole weekend. He was in a terrible mood and couldn’t enjoy anything. I was speechless. But my friend was almost as bad.
This is the same girl who constantly complained about how all her friends weren’t that smart or nice and how she doesn’t know what to do with all her free time and money. That girl taught me something. Apparently, there are a lot of rich people who have so few problems, they just make them up. And yes, I’ve seen her Facebook pictures, met her friends, seen her cars, and talked to her long enough to confirm that she probably wasn’t lying.
79. Too Rich to Raise Your Own Kids
I used to be a preschool teacher at a very expensive day care in a wealthy town (I had to commute up to an hour to get there). There were some good parents who had their kids there, but there were a lot of bad parents, too. Many rich people have kids for ornamental purposes: the Johnsons had a cute kid, we need to have one too. It’ll look great at the company picnic!
Many of them are obviously people who do not want or like children and expect us to take over their parental duties. This led to huge problems, like a lot of parents not coming to pick up their sick kids. State law requires us to send the kids home if they have a fever or are vomiting, but many parents obviously put work first. Which leads to another problem…
The law also prohibits us from taking them back until they have been symptom-free without medication for 24 hours, but sometimes a parent with enough clout could complain enough to get around those laws, unless a teacher complained and threatened to report it. One parent tried and failed, and her daughter came back the day after, supposedly all better. Her teacher caught this three-year old girl taking Tylenol her mother had given her, put in her pocket, and instructed her to dose herself so she could hide the fever. Everyone in that class soon got sick. But she wasn’t even the worst case.
Two boys who were obviously developmentally backwards would come in dirty and with full diapers almost every day. A teacher once marked the last diaper she put on one boy before he left out of curiosity, and sure enough that same mark was on the very full diaper he arrived in the next day. Apparently, the daycare workers were the only ones who changed them.
Their parents continually brought them to the preschool in their pajamas, sometimes without shoes, for an eight-hour day that includes outside play, with no change of clothes. When called about the lack of proper attire, the mom just said, “We were in a hurry today; just keep him inside.” We had to explain that there was a whole class of kids, not just him. We don’t have staff to stay inside just with him. And that’s not even the bad part.
These boys were not potty trained well beyond what is normal and would often freak out when someone tried to help them go potty or change them. When changing one of them, his teacher found KY Jelly and other physical signs of abuse. The teacher immediately reported it to the school and to Child Protective Services. This teacher had been keeping records of all these events, and an investigation was done. It was then dropped. And why do you think that is?
The teacher, herself an abuse survivor, was furious and demanded a follow-up from the caseworker. The CPS worker assured her that it was a misunderstanding, she met with them and the parents were not the kind of people who would do something like that. She reminded the case worker about all the evidence she had documented about neglect, and was told, “But ma’am, they have a million-dollar house!” Awful.
80. We Help the Helpless
I worked for a guy who was old money. He was a waste of space. He couldn’t load a stapler. He didn’t bring a knife for his bread, so he stole a co-worker’s scissors. I got him lunch once. He was upset I didn’t get his half Dr Pepper, half Sprite. Like I should have divined that. And he’d throw temper tantrums. Huge ones.
I remember I set him up with a three-day itinerary. Just this gorgeous set up, multiple page folder, every event by the hour. He loses it. Left it in the rental car to the airport. So, I had to anticipate 12 calls over the next three days to tell him where to go. He couldn’t figure out email on the road.
On this trip, there were a few times he had to hand me over to a hotel clerk or registrar for an event because he couldn’t follow my instructions. He was flipping out on me the whole time. He wanted me to overnight him another itinerary for $120 or so on the last day. I explained the situation and the price. So, I did. Then he then complained that I mailed it to him.
81. You’ll Never Look at Squid Ink Pasta the Same Again
I worked at a nice little shop that sold fresh house-made pasta and ready-to-go sauces. We got the stereotypical rich people due to our location in the middle of Marin County, California. This was in the late 80s and food trends were plentiful and rapidly evolving. Many people were very interested in being on the cutting edge of the latest trend, be it the latest hot restaurant or that month’s fabulous must have menu item.
Not that they were actually into food, but just to be “in the know” and brag about how you simply must try the most fabulous tiramisu at the buzziest place in town. We regular folk would stoically refrain from rolling our eyes in their presence and carry on. So at the pasta shop one evening, a typical Marin matron arrived in her gemmed slippers, clattery jewelry and a cloud of perfume.
She pushed past the other patrons in front of her and said she needed some squid ink pasta. “I’m sorry,” I replied, “we don’t actually make a squid ink pasta, but you may be able to find it at another fancy grocery store in the same plaza. They carry several quality imported items.” She gaped at me and started moaning, “OHHHH NO NO NO NO NOOOOO.”
Of course, now everyone in the place was staring at her. She then told me that she had to have squid ink pasta because she had her “gourmet friends” coming for dinner and they had to have squid ink pasta. I apologized again, explaining that we didn’t make squid ink pasta and again suggested the fancy grocery store, only to be cut off by her loud wailing “OHHHH NO NO NO,” again.
I just stood and watched along with everyone else in the place as she paced up and down before the display case, clutching her head and repeating, “Squid ink pasta…gourmet friends! SQUID INK PASTA…GOURMET FRIENDS!” over and over at the top of her lungs, as if this incantation would magically call forth a hidden cache of squid ink pasta.
Needless to say, we could not provide said squid ink pasta, so I don’t know what she served to her gourmet friends that fateful evening. The whole thing was just so bizarre and over the top. Anytime we encountered some delusional, entitled weirdo, we’d mutter “Squid ink pasta!” and cackle to each other.
82. The Classic “Do You Know Who I Am?”
I work at a classical music and theater venue. It’s in the middle of the city so we ask a small fee for parking. It’s significantly less than what you would pay to park in the street, and it’s clearly marked at the entrance. A guy came up to me with his parking ticket and the first words out of his mouth were, “Paid parking? Do you know who I am?” I did not, none of my colleagues knew, and to this day it’s still a mystery. But he was parked in our parking lot, so yes, paid parking.
83. Saying Please and Thank You Goes a Long Way
I am a cocktail server at the huge pool of a 4-star hotel. A woman once told me, in a monotone voice and without any eye-contact, “I lost my sunscreen. Find it.”
84. Jet Set and Sick of Him
I’m an aircraft mechanic (A&P) and I used to work on the Gulfstream jet owned by a very big multinational corporation used exclusively by the CEO. At the time I was there, the CEO they had was a little… odd. Keep in mind this thing costs tens of thousands of dollars an hour to operate when you divide acquisition costs, maintenance, fuel, and crew salaries with the number of hours flown.
He would have three meals brought on board for himself, so he could choose what to eat in flight. Maybe steak, instead of lobster today. But he would order a tray of sandwiches for the crew or non-VIP passengers, like his assistant. If the flight was less than one hour, he would forbid the crew and passengers from using the lavatory, to save the pump out fee. A pilot once violated this because he really had to go, and he was fired.
He would sit in the back, so he could watch the other passengers and make sure they continued working instead of looking out the windows on company time (even VPs). And my favorite, because it affected me: When he arrived for a flight, all maintenance personnel had to literally hide in tool storage until he was on board (and out of our line of sight) because the mere sight of maintenance people made him nervous about flying.
85. Guessing This Guy Never Listened to Kenny Rogers’ “The Gambler”
I play poker for a living and every now and then some rich guy will sit down and start going all in every hand for $300-$500 without looking at his cards. I was in a game where a guy was betting $1,000-$3,000 without looking at his cards. It was insane to me, but for him I guess it wasn’t that much money. Really nutty.
86. Hospitality Is a Two-Way Street
I work at a very expensive hotel in Hawaii. Something that happens all the time with entitled or rich people is that they will just come up to the desk and yell words at you. Like no hello or please, just “Luau” or “ATM.” It’s like they aren’t even thinking of us as people.
87. Spend Like You’re Going Broke
The rich guy I know was completely delusional. He walked around and bought items like he was a prince. Spent $1,000s on clothes in one sitting and would buy drinks for people at the bar. His bills were examples of the “rich and don’t care” attitude. Then one day he asks me to print out his banking info and credit score. Turns out he was $100,000 in debt, despite pulling in a six-figure salary. His spending habits were insane.
88. Like the Lonely Island Song?
I interned at a production company. The CEO made me go get a new Blackberry for him. Took four hours to go downtown because it HAD to be bought in downtown LA for whatever reason. When I brought it back, he opened the plastic, turned it on, and asked “What the heck is this? Why aren’t my numbers on it?” When he was told it was new, and so of course it wouldn’t have his numbers, he threw it on the ground. Literally just smashed it. I was flabbergasted.
89. This Woman Is the Literal Worst
I work at a ridiculously upscale steakhouse in Manhattan as a hostess while juggling being a college student. We have some of the most demanding and exclusive clients come in daily and I have a lot of stories. Our guests range from Michael Cohen, Steve Madden, Anderson Cooper to lesser-known Real Housewives stars and just filthy rich businessmen and women.
Last winter while at work, we had three hostesses at the podium. One for seating people, one for checking in, and one for checking coats. I was checking coats (tips are unbelievable) around 7, when our place is incredibly busy and hectic. Well, a lady checks in with her husband and hands me her coat. I hand her the ticket number for her coat and then proceed to hang it up and mark it with all of the other coats in the closet.
In the closet, it was mainly mink coats during the winter, easily upwards of $15,000 from brands like Moncler, Burberry, Gucci etc. Her coat was a Moncler. It’s easy to remember in the moment who had what coat, but after checking in 200 other coats I totally forgot what kind of coat this woman had, and she was not a regular client so I didn’t make a special note.
Fast forward two hours later, they’re leaving. She hands me her ticket and I go to get her coat. I come back to hand it to her and she looks at me puzzled and goes, “That’s not my coat.” I go, “Oh okay, are you positive? What did your coat look like by chance?” She sniffed and said “Seriously isn’t it your job to know that?”
So I asked her to come to the coat closet with me so we could locate her jacket. She wrinkled her nose and told me I was a joke for not being able to do such a simple job! I apologized and walked her to the coat closet. We searched high and low for about an hour for her coat and at that point, she was screaming at me, every nasty name in the book.
I stood there, calm as could be, because the money was worth it. I finally decided to involve the manager because I just did not know what to do. He didn’t know what to do either, he said we would reimburse her for the cost of her coat and we would write a check but she refused. She must have tried on all 200 coats in our closet and claimed that none of them were hers.
I was petrified at this point that I had given her coat away to someone else, as many look the same. She then told me I would be getting a bill personally from her lawyer and I was actually scared because I knew how expensive those coats were. She berated me and degraded me in front of the manager and told him that I need to be fired.
Finally, she had enough and said since you gave my coat to someone else give me the coat you initially gave me because I can’t go outside without a coat. And at that point I didn’t care anymore. So, she takes the coat I initially gave her, puts it on, and says, “Wow it fits perfect.” She reaches in the pockets and asks, “How did this coat happen to have my wallet and keys in it too?”
I looked up and literally had no words. I wasted about two hours being belittled by the woman, when I was right the whole time. The lady was like, “I don’t know what to say” and my manager said, “You owe her [me] an apology.” And the lady handed me her wine glass, a $1 tip, no apology, and left like nothing happened!
I sat down on the closet floor and cried my eyes out. I had been awake since 5 AM for school and was the closing host that night, which meant I wouldn’t be leaving until about 2 AM, getting home around 3 AM, and waking back up at 5 AM for school! She wasted what little energy I had left and made me feel so worthless. My coworkers were awesome though, the bartender made me a drink and they all gave me a hug.
90. Don’t Ask, Don’t Dry Clean
I used to work for a company hosting luxury car driving events, where the customers came for a week or a weekend to learn to drive the latest models on ice. Most of the customers were polite or even nice, but whenever we hosted the Russian groups, everyone knew all bets were off.
These guys had never heard a “no” that couldn’t be turned into a “yes” with a wad of cash. The most memorable incident was when two of them flew in three (assumed) Russian prostitutes, and had their driver drop said prostitutes off at the airport the next morning just before picking up these guys’ wives from the same airport. I was told by the cleaning staff that the room they’d used was covered in blood and feces, amongst other things.
91. Spite Trip
I drive a limousine, often for wealthy clients. My least favorite are the children. One of my spoiled trust fund clients once insisted on picking up four friends from different areas of town. He convinces these people to go to the bar with him, but when we get there, he kicks them out and has me drive him to the airport, where he picks up a last-minute flight to Vegas.
92. The Nerve of Some People
Someone had a heart attack on the patio of our restaurant. Paramedics came and were assessing the situation and trying to prep the guy to go to the hospital. This woman dining with her husband decided very loudly to ask my manager in her best condescending rich person tone, “Is this going to take much longer, we were enjoying lunch.” The restaurant goes dead silent and her husband looks like he’s about to puke from embarrassment. They were politely asked to leave and never come back.
93. More Income, More Intergenerational Problems
My mom works in a family-owned business, and while the owners aren’t excessively rich they’re definitely 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 away 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.
94. To the Batcave!
I knew someone who traded in his Porsche and bought a new one every year. His parents were wealthy, died when he was in his teens and left him a multi-million-dollar trust fund. What was sad was that he felt that he couldn’t pick up women without flashing his cash and expensive sports car, but he would dump them all in a couple of weeks because “they were only into me for my money.” Loneliest guy I ever met. He is not Batman, by the way. His parents died in a car accident and his butler’s name is Davin, not Alfred.
95. Sometimes It’s Best to Keep Your Mouth Shut
Company consisted of something like 1,200 employees at the time, and rented out a big conference center for a Christmas party. At the opening of the party, the CFO was giving opening remarks, and asked—expecting cheers—if everyone liked their Christmas bonuses. He got booed. See, of that 1,200 people, a bit over a thousand were in customer service.
No one in customer service got bonuses, only people in the “corporate” departments got bonuses. And our awesome CFO decided to rub everyone’s noses in it, because clearly the Chief Financial Officer of a company would have no idea that 80%+ of his company didn’t get bonuses. At the same party, the CEO made an announcement that the company would be closed on Friday (Christmas that year was on a Thursday), and everyone got a day off.
Now, he had literally just finished making a speech about how everyone was important, and everyone was part of the company, no matter the department. He had shoveled crap hard, trying to make CS happier. The next day, we all got a memo that Customer Service still had to work on that Friday. We apparently didn’t count as “everyone” and the CEO just hadn’t realized that the announcement wouldn’t apply to anyone. January saw a 60% attrition rate.
96. VIPs: Very Irrelevant People
I worked at a nice restaurant in downtown Portland, and one day a lady called to make a dinner reservation for a large group. But first, she starts asking all these questions about “security” (we had none) and how I thought the staff and patrons would handle a “celebrity” dining there. Is there enough space to be private? They like to be private. Would it be okay if they brought their own security, to stop people from taking pictures and such? But of course, she couldn’t name names.
I rolled my eyes, gave her the go-ahead to do whatever they needed to do, and booked the date and time. Yes, I was super curious who it would be, and stayed past my shift to see who walked through the doors when the big night came. The group arrived, and it was…no one. Not one of us who worked there recognized a single member of their party.
They sure acted like they were someone, but all we saw was a loud group of douchey-looking twentysomethings. They actually did bring a “bodyguard,” who stood in the corner with sunglasses on the whole time. The only attention they got from other diners was the occasional side-eye because they were being such rude and obnoxious nitwits. Shock of shocks, they treated our staff horribly and tipped even worse. I will never know who that person thought they were.
97. A New Meaning to Filthy Rich
Worked IT for a small company, the boss was Mormon and so every nine months there was another kid running around. One day, he called me at home to drive across town and help him with his home network for some under-the-table money. The neighborhood was gated, and the guard was looking so far down his nose at my 1986 civic that I thought his neck would break.
The house was HUGE, but I knew something was wrong the moment I walked in the door. I have never seen such filth, I had no idea people could live like that. “The maid hasn’t come yet, sorry for the mess.” Yes, that man just said they use a maid service, so this was likely just a single week’s worth of filth. The high chairs in the dining area were absolutely surrounded by garbage and food, dirty clothes everywhere etc. I guess when you have money you don’t even need to clean your room anymore.
98. 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 illegal 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.
99. With a Little Help From My Housekeeper
There was a kid at my high school. When he was 14, he had a learner’s permit, but his parents got him a Mercedes-Benz G-Class. Every day, he drove it to school and was determined to park it in the parking lot to show it off. So, he had his housekeeper drive to school with him and the housekeeper’s son drove a car behind her to take her back home—which was only about two miles away from our school.
100. Low-Class Attitude
I was briefly an assistant to a CEO of a large company in my country (I live in Northern Europe), and this guy was a real jerk to everyone. I just made coffee, ran with mail, and copied things. I say “briefly” because I only worked there for three weeks. I made an honest mistake, copying the wrong documents, resulting in a brief embarrassment on his side in an in-house meeting with some of the other big guys of the firm.
I got called into his office and, knowing his history with previous assistants, I was visibly nervous. He then began absolutely shredding me for 15 minutes, completely red in the head, spit flying in my face as he stood above me, basically ripping me a new one. I started crying (This was my first job, and I was 15 at the time), and he stopped shouting. But that wasn’t a good sign.
He took one finger to my chin, lifted my face up so I looked straight at him, and then he said “You’re a nobody. Don’t you ever forget that.” And then he threw some paperwork at me to let me officially know that I was fired (which I then had to pick up from the floor), and then he yelled at me to get the heck out of his office.
101. A Costly Choice
I was invited to a graduation party, hosted by a very wealthy couple whose daughter had just graduated from Yale. Her father came out, in front of the guests, displaying his Rolex and Cartier watches—asking which one of the two expensive watches the group thought would be “the more appropriate for the occasion.” Everyone just looked at each other, silently—not quite sure what to say.
102. Small Business, Big Problems
I work at a small business. 20 employees +/-. My wealthy boss made a big speech about austerity measures and no raises this year. A week and a half later he drives up in a brand new Silverado with all the bells and whistles. Expensed to the business of course. He would hate to have to pay taxes on those profits. One of the less subtle members of the staff took a literal dump in front of his office door.