Generally, stereotyping is a rude and foolish thing to do. However, in some cases, people’s behavior fits a stereotype so perfectly that it reminds you where the cliche comes from. We need a way to predict the actions, likes, and dislikes. of new people, after all, and a stereotype is a good place to start.
One of the most pervasive and (unfortunately) accurate stereotypes is that of the quintessential “rich person.” Many of us have interacted with a rich person who almost seems like a caricature of privilege because their actions and mannerisms fit so well into what the stereotype predicts.
This article is full of stories written by staff at high-class establishments, sharing the time some millionaire guest did the most stereotypical “rich person” thing they’d ever witnessed.
45. Snapping And Not Looking
I was at a nice hotel in Berlin, eating breakfast, and there was a couple next to us — a man behind his newspaper, and a woman reading her iPad.
The man did not look up from his paper, but actually reached his hand way above his head and snapped to summon the waiter. And when the waiter didn’t appear within a nanosecond, he lifted his hand higher and double snapped. He didn’t even look at the waiter when he arrived, just ordered from him around his paper.
44. Lucky Person Next To You
I interviewed at a large hotel attached to a casino, and while I was being shown around the front desk, a woman walked up, said nothing, and got room keys after being greeted by the front desk agent. She immediately turned and walked away.
Then the manager who was interviewing turned to me and said, “That’s Mrs. Richladypants. You never ask her for her name, her ID, or god forbid a credit card. She stays here comped once or twice a week because her husband spends so much in the casino. If you upset her she will yell at you and then hand the person working next to you a $100 bill just to spite you.”
43. Money For All
My uncle works at a very upscale restaurant on a very well-to-do and desirable vacation island in the Atlantic Ocean.
One of their regular customers is a billionaire oil guy. My uncle has told me that if he really likes the meal, he will go through the restaurant and, in front of everyone, peel off crisp $100s from a giant roll of money in his pocket and tip every service person whether they helped or not.
42. Cook Faster, Newbie
My brother was an apprentice cook in one of the most prestigious hôtels on the French Riviera. That week he was assigned to prepare the free tapas/amuse bouche they were giving at the hotel bar for customers.
This super famous french actor came in. He played a lot of comic roles, so there’s this pleasant aura around to him. All day long he requests more of the free appetizers. He was getting mad at my brother when he didn’t prepare them fast enough because he was hungry. It totally changed our view of the guy in his movies.
41. The Salmon Lady
A million years ago I worked at a restaurant, and we had a woman who would come in once or twice a week and order the same dish with a ton of modifications. She always had the server change the plate, linens and silverware when she got there, and had other oddities that I can’t remember. None of this was a food allergy; they were all just quirks.
We eventually made her own code in the computer for “Salmon Lady”, and as soon as she came in, the hostess sent that order to the kitchen.
40. No More Servant’s Quarters
When I was working nights at a ritzy hotel many years back, a lady came in to reception. I say ‘lady’ because she definitely was — she just reeked of old money. She had a guy in tow, wearing a grey suit. As this was about midnight on a Friday, I immediately clocked him as a chauffeur/aide type deal. No problem, I’ve seen that before.
She asked if we had a room for the night. “A decent one, please. A suite, ideally.” No problem, we had a suite available. I told her the price — as night manager I had the freedom to charge pretty much whatever I liked, if it meant making a sale. But for her I charged full price. Screw it, she looked like she could afford it. She didn’t bat an eyelid.
Then it came to her chauffeur guy. “Do you have a servant’s quarters for my driver?”
“Um, no, sorry madam. Just the standard rooms.”
I gave her the price for one of our standard rooms, and she screwed up her face. “Oh no, that’s too much. Don’t you have, like, a staff house or something he could stay in? I’d really rather not spend money on an actual hotel room for him.”
She said all this with the guy standing right next to her. I felt really bad for the poor guy and wondered if this was usual for him.
39. Make A Mess, Pay For It
A wannabe rap crew was in town for a music video they were shooting. Their leader was the only guy with money; the rest were just followers.
He threw an expensive bottle of wine on the floor and had his friends videotape him making gang signs over the mess; this rapper was not happy and neither was his they when they found out what it cost. It was only $200, but they refused to pay for it! Not because of the price but because they honestly believed they didn’t have to pay for it if they didn’t drink it.
38. Picky Sleeper
I work at a luxury property in California, and we had the co-founder of a large payment processing company stay with us a while back. 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 the 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.
37. Pay For The Waste
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 how the waiter wastes all of it by pouring it down the drain (some places let you do it yourself).
Sadly, it’s an established thing in these kinda circles, like, it‘s on the menu cards and all that. Honestly the dumbest way of flexing I‘ve ever witnessed.
36. “Celebrity” Experience
I worked at a nice restaurant in downtown Portland. 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? etc. But of course, she couldn’t name names. I rolled my eyes, told her whatever she needs 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 snooty-looking 20-somethings. They actually did bring a “bodyguard” who stood in the corner with sunglasses on the whole time.
35. Remove This, I Have Better
Had a business dude rent one of our apartments for 3 weeks at this fancy hotel I worked at. On the second day, we get a maintanence call; he wants us to remove the TV. Not replace it, just remove it entirely.
The housekeeper I went up with maintenance to clean up any mess from the move and got to see it all. The guest was removing our TV — because he went and bought his own. Bigger. Flashier. Brand new. There was also a brand new (I cleaned up the packaging) PS4 he was hooking up to his new TV.
34. The Freshest Batch Possible
Ms. Linda came by our swanky Starbucks in her old school Mercedes around 4:45 am every morning (we opened at 4:30) accompanied by her dog. She would INSIST we brew a new batch of coffee when she ordered it or else it wouldn’t be fresh. Given her consistency, we eventually just started waiting until 4:45 to brew our first batch. 4/5 times she would take a sip and ask us to brew a new batch. All while sitting at the drive thru window.
Granted, there was almost never anyone behind her, but it meant she could watch me grind new beans and wait the full 5 minutes for it to brew. She wouldn’t accept a pour over cup, nor could we take coffee from the urn before the full batch finished brewing.
33. Better Bathing Through Money
I worked at a private villa in Bali, where one guest stood out. She only drinks and bathes 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. She wore sunglasses at night.
32. Too Rich To Be Picky
I used to work in a luxury hotel. A colleague of mine got a call from an in-house guest asking for a car to take him somewhere. Naturally, my colleague outlined the options. The guest got annoyed and hung up.
A few minutes later, the guest came down to the front desk and asked for my colleague. He then proceeded to show him a cardboard bag literally overflowing with cash, and started saying, “You dare ask me which car just because of different prices? Can’t you see how much money I have? Why do I care, just get me a stupid car ready.”
31. No Swatting Service
Worked in a fancy schmancy lobster pound/restaurant on the water that had a lot of outdoor seating. These very very wealthy people come to eat and demand a table outside for dinner.
Now, it’s just before sundown in the middle of summer in Maine and we’re on the water, so mosquitoes are definitely not scarce. These people sit down, order a $200 bottle of wine, a massive lobster each, and some appetizers. They seem to enjoy the meal up until the sun sets and the bugs come out.
These people were not happy. They kept complaining and complaining about the “crappy restaurant not paying for mosquito spraying.” The waitress lit them a couple of candles and asked if they needed anything else. Those jerkwads actually asked her to stand next to them with a flyswatter. She laughed, thinking they were joking. But the man said, “Whatever happened to good service nowadays?”
They left no tip on a $350 bill.
30. Elderly Cookie Tantrum
I’m three years into being sous chef at a private resort in Upstate New York. Most of our guests return generation after generation. Wealthy, very wealthy. We get some Congressmen, actors getting away from the daily grinf. But mostly families that are crazy rich, and four generations deep into annual visits.
The number of requests we receive are insane. But one that stands out… A 60-something-year-old woman crying as loud as she could because we didn’t have the cookies she wanted. Guys, you would’ve thought she was just told someone had died. She made a huge scene in the dining room. Her husband had the backbone of a jellyfish and just sat there trying to console her. “It’s ok honey. I’ll get you cookies. Don’t cry.”
The owner went out and bought her the cookies because we do not have time for that crap.
29. Steak, Wine, And Complaints
I worked at a restaurant in the lobby of a rather nice hotel. There was a rich dude who basically lived there. He would eat in our restaurant every night, so our chef had to hand-pick his steaks from a local butcher. The steaks were absolutely massive and always specially prepared just for him.
Still, every single time, this buttstain 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 our cheap wine that we served by the glass. However, he would request that we 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.
28. Never “In The Red”
My former boss (insanely wealthy), used to stay in presidential suites and would have any and all things red removed. He was a high roller at several casinos and they made special chips just for him as a substitute for the red ones. He hated the color red because when you’re losing money, you’re “in the red.”
27. Thank You, Rich People!
Ordering the most expensive wine in the house… pouring two 1/2 glasses… taking a sip… and sending it back knowing full well they are never getting a refund.
To those folks I say THANK YOU! Nothing makes employees happier than free (expensive) booze.
26. Even Rich Kids Would Rather Play
These people threw a 6-year-old’s birthday party at a tapas restaurant called “______ Wine Company.” They tried to feed the kid tartare but this poor boy kept asking for balloons and French fries. Then they tried to give him jalapeno creme brulee for dessert, quizzing him on how to pick out scents in wine. They just sighed when the kid didn’t seem interested, and kept ordering more wine until he feel asleep in the booth. Afterward, the woman complained to her in-laws about how exhausting motherhood is.
25. Ice, Ice, Richy
They made me take their waters back, dump out the glasses, put ice in the bottoms, add water, dump out the water but keep the ice, then fill the glass up with water again. I just went to the kitchen and walked out with the same glasses.
24. Natural Soundtrack
I worked abroad at a high-end beach club in Greece. All our clients had to speak English as all the staff were Brits. Now, this place was fairly ritzy; tabs were often £20,000 after a week — that kind of place.
I worked all over but mostly in the restaurant. The best rich person thing I saw was when we were asked to turn down the volume of the insects in our outdoor restaurant.
23. Sharing The Nectar
I used to work at a high class hotel restaurant, and one of the regulars there would always order VERY expensive bottles of wine. I’m talking about top-quality, expensive stuff, rare and delicious. He would always go through the same routine: He’d order the first bottle, taste it, and declare it either corked or just plain bad.
He would then call the manager and tell him he would still pay for the bottle on the condition that all the serving staff would take turns tasting it at his table so they could “learn what makes a wine taste bad.” Remember, we’re talking about wine bottles worth in the hundreds if not thousands. He would then order his own bottle and drink that one.
Thing is, the first bottle was perfect. Both the sommelier and the waiters were in on it. Only the manager didn’t (officially but probably did) know about it.
So every now and then, we could have a taste of wine worth a couple of dozen dollars a sip just because this guy had his routine, wanted to teach us about wine, and was loaded with money.
22. Magical Rich Chanting
At the pasta shop one evening, a typical rich lady arrived in her jeweled 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 (fancy grocery store in the same plaza). They carry several very good imported items.”
She gaped at me and started groaning, “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….”
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.
21. Classically Trained, No Pop Knowledge
So I’ve played at a lot of these venues with rich clientele, but the one that takes the cake is the rich buttwaffle that comes and demands we play [Insert Pop Song on the No. 10 Billboard] because his little princess likes it. Now while we have taken requests before, what’s difficult here is that my fellow colleagues and I, professional string musicians, are getting paid by the venue to play classical music that we have pre-agreed on and prepared. My colleagues and I do not know the melody nor harmony nor even the bloody key of generic pop song No. 7.
20. Just Keep It
Oh man, this foursome came in to the restaurant I worked at (rated the best in the state, consistently), spent a ton of money, tipped 50% on the bill, and then the guy who signed the check proceeded to leave a $300 Cartier pen in the book. I ran out to the valet stand to return it, but he just laughed and told me to keep it.
19. Late And Cheap
My dad used to work as a valet for Lawry’s in downtown Chicago. Some pretty well-known football player came in about 15 minutes before closing with a group of friends. He made them re-open the kitchen so they could all have steaks. Then they stayed for almost two hours after close being really loud and obnoxious and rude to most of the staff. He also tipped everyone horribly, especially considering everyone had to stay later because of him.
18. Your Servant Wasn’t Friendly Enough
A man called in an order at 9:57 pm, when our store closed at 10. I knew that delivery was going to keep me in the store an extra half hour to 45 minutes than usual, time which I would not be paid for.
So I deliver his sandwich, and apparently when I delivered I wasn’t as friendly as he thought I should have been. He had paid via credit card using the app, so his tip was already included in the bill. He was so incensed at my awful and rude behavior that he called the store, making me stand there and wait while he did it, and demanded that my manager refund the payment, saying that he would pay in cash instead.
My manager was generally pretty laid back, so he just went along with it despite it being an unorthodox request. The man then paid me in cash with exact change, thereby denying me my tip, all because I wasn’t as friendly as I should have been. I won’t name him, but he’s a well known billionaire in my hometown.
17. Unappreciative Of The Finer Things
I used to be a bartender. One night I had 4 guys walk up to the bar and order 4 shots of Remy Martin Louis XXIII… which was $435 a 1.5 oz pour.
It’s normally poured into a snifter and a discerning drinker will usually dilute it down slightly because it’s between 40-100 years aged and is like 55% alcohol by volume.
These four rich bros didn’t know any of that and wanted it in shot glasses. They then proceeded to throw back $1700 worth of the finest cognac you’ll ever taste.
They tipped me $300 so I forgave them quickly, but that was such a rich person thing to do.
16. Working For A $50
I worked at a Hilton for a little while, where I made about a dime above minimum wage cleaning bathrooms, walkways, polishing brass handrails etc. On duty, I walked around with an obvious cleaning cart and was not service staff.
Once, at about 2 am, this obscenely rich family barged in fighting with each other, generally being jerks, and their airport shuttle driver was hauling in case after case of luggage — the poor guy. The matriarch of the family snapped me over (pushing a custodial cart), threw a $50 bill at me, and barked at me to have the luggage brought to their room.
Then they laughed at me for bending over to pick up $50 and laid the rich attitude on thick.
15. Only The Finest Turf!
A very famous older actress/singer who once played a witch stayed in one of these hotels for a week or two with her pet dog. She demanded that a mini set of stairs had to be built so her dog could get up and down the bed. She also demanded that her balcony had fresh rolls of turf fitted everyday so her dog could poo and pee on it; it also had to be fitted when she wasn’t there so sometimes I had to sit around for hours waiting to install the rolls.
14. All Help Is Worthwhile
I worked at a 5-star hotel. This one guy would come in a lot — no small talk though, straight to business. If you helped with anything, it was an automatic $20. Open a door? Help with a bag?Anything you did was $20. Walking in and out of the hotel, he probably spent around $120 every single time.
13. Try Your Work
Two other colleagues and I are on shift at our restaurant. We prepare everything for this one rich customer and send it out. Twenty minutes later, the waitress serving the guy says he requested 5 clean knives. It seems this guy had tried a bit of everything, then proceeded to cut a layer off the part where he’d eaten with a clean knife (hence the 5 knives), so the rest was not contaminated by him trying it.
He said he was full and insisted the food should not be wasted but given to the staff on shift so “they can also taste the great food they make.” When he was leaving, he came to the kitchen and thanked everyone/shook everyone’s hand. We later found out the guy owned over half the resort, apparently.
12. Just Bring It Back To Her
I served a woman her glass of Chardonnay. She said it was wrong, that I had brought Pinot Grigio instead. I brought it back to the bar, asked the bartender what he poured, and he said Chardonnay. I handed him the glass, he looked at it, did nothing, and gave it back saying, “Bring it back and see what she says.” I brought it back to her, she tasted it, and said, “Much better. Be more careful please.”
11. $16,000 To Sit
This couple asked to purchase two of our high rise bar chairs and keep them in the back in case they come in and there are too many people at the bar. This way, they won’t have to wait. Our bar chairs cost $8,000 each. These people wanna spend $16,000 just so they can sit whenever they come in.
10. Difference Between A Hamburger And A Cheeseburger
My roommate in college worked at a private resort/club as a waitress back in her hometown. She would tell me all sorts of stories about how snobby most of her clients were. My favorite story was when a woman asked for “a cheeseburger with no cheese with lettuce, tomato, and mayonnaise.” My roommate took the order and moved on to the next person at the lady’s table.
After she was done taking orders, she reread everyone’s request back to them to make sure they were correct. When she got to the lady’s order, my roommate made the “mistake” of saying, “And, Ma’am, you wanted a hamburger with lettuce, tomatoes, and mayonnaise.”
The woman was livid and said, “NO! I WANT A CHEESEBURGER WITH NO CHEESE WITH LETTUCE, TOMATOES, AND MAYONNAISE!!!” She called my roommate all sorts of terrible names and told her how stupid she was for not knowing the difference between a cheeseburger and a hamburger. Then she mentioned how she hated being served by “lower-class” servers as they didn’t know how to properly take orders.
9. Not Upgraded Enough
I work in a 5-star hotel in Germany. We had guests who checked in and were given an upgraded suite for New Year’s Eve in a special section of the hotel. They complained when they realized they would have to walk two minutes to the New Year’s Eve party. Then they complained that the suite wasn’t good enough to be a suite and insisted they be placed in a deluxe suite closer to the party. We had literally no rooms available. They were extremely rude and pompous to every employee. It was a nightmare for management. They spent thirty minutes arguing before finally saying “FINE!” and keeping the rooms we had given them.
8. Tip For The Month
When I brought the bill after lunch, this rich dude fumbled with and unknown currency, walked off, then walked back, threw about half my month’s wages on the table and said, “Oh yeah, here’s a tip.”
7. Waste Not!
My favorite was the time when a group of four richies ordered a last course at sushi restaurant of $400 in live uni (urchin), ate one piece each, and then said they were full and left the rest. It’s one of the few times I’ve seen waitstaff unapologetically nosh on someone’s leftovers.
6. Fur Baby Inclusion
I worked in a high class restaurant in a nice hotel (by my town’s standards anyway) for a few years. We had a couple come in with their lap dog religiously every Tuesday evening for dinner. Due to the health code, they were not allowed to bring their (non-service) purse poodle into the restaurant. Their solution? Request a special table be set up in a private nook of the hotel lobby so they could dine in style with their fur child.
5. Money Fight
A guest was sitting by himself in the lounge sipping a $39 glass of sparkling wine. The table next to him was six Italians — three couples. The men were drinking beer and whiskey while the women enjoyed a bottle of 2007 Cristal ($795). The ladies were admiring the view by the solo gentleman’s table so he complimented their choice in Champagne.
“YOU DON’T-AH SPEEK TO MAH WIFE,” exclaimed one of the husbands.
“I can talk to whoever I’d like,” the man replied.
“YOU DON’TAH EVEN LOOK AHT MAH WIFE,” the husband hollered, followed by shouts in Italian at the women to come back to the table.
“YOU DON’T SPEAK TO ME THAT WAY, DO YOU KNOW I AM?”
“YOU-AR-A NOBODY! I HAVAH BILLIONS AND YOU-AR-A NOTHING”
“SIR, I AM A BILLIONAIRE. YOU HAVE NO IDEA WHO YOU ARE TALKING TO OR WHAT YOU ARE TALKING ABOUT.”
Now at this point, the hotel security shows up. They awkwardly intervene, which turns the billionaires’ wrath on them, leading to grown men screaming at other grown men about their paychecks and genital sizes.
Finally, the solo guest agrees to leave (not because he was asked to, but because he decided to), and these two men go to shake hands at the urging of the wives. As they come out of the handshake, the solo guest finishes — “I OWN THE ***** HOTEL! IF I EVER SEE YOU IN THERE I WILL PERSONALLY THROW YOU ON THE STREET!”
The only thing missing from this billionaire fight was them throwing wads of cash at each other.
4. Wouldn’t Want To Be Rude!
I operated a premium chain restaurant in Canada. One day this Indian gentleman started coming in, at first by himself. On the first day he spent $200 on wine and tipped $1000. The next day he did the same again. When we saw him the third time I had servers fighting over him.
Anyway, one evening he got drunk on wine and Brad the busboy made the mistake complimenting his watch. Mr. S. takes off his Tag 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 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.
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.
3. One Expensive Meal
I worked for a resort in the Seychelles for 4 years. I have hundreds of stories which would fit this post, but one that stands out was a very wealthy Canadian family who stayed at one of the private residences for a couple of weeks.
They brought their own staff including two personal chefs, but also asked for a hotel chef to assist their team with prep and local ingredient knowledge. A chef I was friendly with was selected to spend the two weeks with them.
One day, another member of their staff came down to one of the restaurants and purchased two bottles of wine for €11,000 each. Now, we had far more expensive bottles on the list, but this was still a notable sale. So later that night, I asked my mate what they had cooked to accompany the wine.
Turns out they had poured both bottles into the pot while making a Coq au Vin.
2. Peasant Rebellion
I once saw a Wolf of Wall Street type character trying to impress his flock of sheep in an expensive bar. He approached the server and abruptly ordered a round of expensive whiskeys. He then pulled out a wad of $100 bills and extended his arm to her saying “TAKE SOME, PEASANT.” The whole time, he refused to look at her, instead smiling at his friends for approval. The server took the opportunity to teach him a lesson.
She swiftly knocked the entire wad out of his hand and I took great pleasure in his angry reaction while he scrambled to pick up the cash in a crowded bar.
1. He Was Enjoying Life
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 lady who was dining with her husband decided very loudly to ask my manager in her best rich witch tone, “Is this going to take much longer? We WERE enjoying lunch.” The restaurant went dead silent. Her husband looked like he was about to puke from embarrassment. They were “asked” to leave and never come back. It’s nice when rich jerks suffer some consequences.