The insanely rich seem to live in a whole other reality. With great wealth can come great ignorance, excess, and just plain insanity to us 'poor' folks. And no one knows this better than those who have to work for or serve the financially elite.
We combed through Reddit searching for such tales, gleaning a ridiculous insight into how the top 1% really lives. Content has been edited for clarity.
They Were Too Rich To Understand How Ridiculous Of A Request It Was
“I worked in a fancy schmancy lobster pound/restaurant on the water that had a lot of outdoor seating. These very wealthy people came to eat and demand a table outside for dinner. Now it’s just before sundown in the middle of the summer in Maine and we’re on the water so mosquitoes are definitely not scarce. These people sit down, order a $200 bottle of Pinot and 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 and complaining and complaining about it and the ‘terrible restaurant not paying for mosquito spraying.’ The waitress gets a couple of candles to light and asks if they need anything else and those rich snobs asked her to stand next to them with a flyswatter. She laughed thinking they were joking and the man said, ‘Whatever happened to good service nowadays?’ They also left no tip on a $350 bill.”
Generously Lavish Gifts
“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 one bottle of Malbec 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 had a little too much to drink and Brad the busboy made the mistake of 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 overdid it 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.”
She Wanted Him To Sleep Where?
“Working nights at a hotel many years back – not super high class, but certainly no budget hotel either – a lady came into 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. Oh well, 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 frowned 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.’
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.
After a few more questions and her considering whether to have him sleep in the car (yes, really), we eventually settled on him having a standard room for rock bottom price (I think about £30 or so) – that was as much as she was willing to spend on him, and less than a tenth of what she was paying for her own room. To be honest, I’d have given him a room for free rather than having him sleep in the car – but clearly, I had more compassion for the guy than she did. It wasn’t so much her cheapness that got me (although it did), it was the way she was talking about him with him stood right there, like he was a piece of equipment she didn’t want to pay storage for rather than an actual human being.”
Waffle House Benji’s
“I’m loosely acquainted with someone who is obscenely rich. He dated my best friend for a while back when we were in college. As you can imagine, he bought her fancy things all the time, took her on expensive family vacations with his folks, etc. He was a stereotypical rich kid, but he was also kind and still very down to earth.
They dated about a year and in the spring we went spring breaking in his family’s condo at a famous spring break beach location and there was just me, my best friend, him and a couple of his friends. The group decided we wanted good old fashioned Waffle House breakfast after a night of revelry. After eating, I noticed he was lingering behind the group. He’d said he had to take a leak, but he stopped back by the table on his way out to the car. Curious, I ran back to the restrooms just so I could pass by the table to see what he’d done.
He left the waitress a small pile of Benjamins as a tip. Had to be 4 or 5 hundred dollars. I couldn’t quite tell because they were folded and rumpled from being in his wallet.
My mouth fell open when I saw it and I forgot I was even heading to the restroom. I looked out by the car and he was watching me through the glass windows, held up his finger to his lips mouthing, ‘shhhh,’ and beckoned me back out to the car.
I didn’t tell, but my eyes were glued to the table as we pulled away in his car. The waitress collapsed into the seat of the table when she saw it. Pretty sure she was crying.”
It Was A Moncler Mink Mixup
“I work at a ridiculously upscale steakhouse in Manhattan as a hostess and we have some of the most demanding and exclusive clients come in daily. 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 3 hostesses at the podium. 1 for seating people, 1 for checking in, 1 for checking coats. I was checking coats (tips are unbelievable, UNBELIEVABLE!!). It was around 7 pm, our busiest hour and we usually do around 300 covers per night and we have an entire bar apart from the restaurant side so it is always hectic. Well, a lady checks in with her husband and hands me her coat, I hand her the ticket number for her coat then proceed to hang it up and mark it with all of the other coats in the closet. In the closet was mainly mink coats during the winter (easily upwards of $15,000 and more) Moncler, Burberry, Gucci etc. Well her coat was a Moncler coat. It’s easy to remember at 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. Well fast forward 2 hours later they’re leaving, she hands me her ticket and I go to get her coat and when I come back I hand it to her. She looks at me absurdly, glass in hand and goes ‘That’s not my coat.’ I go ‘Oh okay, are you positive? What did your coat look like by chance?’ She scoffed and said ‘Seriously? Isn’t it your job to know that?’ So, I asked her to come to the coat room with me so we could locate her jacket.
She berated me and degraded me in front of the manager and told him I need to be fired! Finally, SHE had enough and said well since you gave my coat to someone else give me the coat you initially gave me because I can’t go outside with no jacket. And at that point I was like forget it take someone else’s coat I don’t care at all 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 says ‘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 2 hours now 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.’ The lady handed me her empty glass and a $1 tip, no apology and left as if nothing happened!
I sat down on the closet floor and poured 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 2 am ish and getting home around 3 am and waking back up at 5 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.”
Some Of Us Can Only Dream Of Spending That Kind Of Money!
“I worked for a resort in Seychelles for 4 years. I have hundreds of stories 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 vino for €11,000+ each. Now we had far more expensive bottles on the list but this was still a notable sale and later that night, I asked my mate what they had cooked to accompany the bottle.
Turns out they had poured both bottles into the pot while making a French dish of chicken called Coq au Vin.”
They Were In For A Rude Awakening!
“I worked at a Hilton for a little while. Made about a dime above minimum wage cleaning bathrooms, walkways, polishing brass handrails etc. I walked around with an obvious cleaning cart and was not service staff.
Once, about 2 am, this obscenely rich family barged in fighting with each other, generally being brats, and their airport shuttle driver was hauling in case after case of luggage, poor guy. The matriarch of the family snapped me over (pushing a custodial cart) and threw a $50 bill at me, and barked 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.
I went ‘Yes ma’am I sure will!’ Wheeled my cart away and took a nap in the way back of the laundry room behind the machines. Oh man, it was so warm and noisy – you could sleep off a nuclear bomb. I miss that spot.
The family wanted my head when their luggage was still in the lobby the next morning. Fortunately, I was so anonymous and unworthy of their attention they couldn’t describe me, and the camera worker in security was too hungover to care.”
“I Can Buy And Sell Every Person In This Room, So I Have”
“Around 10 years ago, I and my best friend worked for a hospitality company specializing in sporting events. This particular time we were working at a high-class horse racing event tending to the owners and shareholders. One particular owner was very snotty to the two of us but we had to grin and bear it all while he bought £500 bottles to drink a single glass and have us throw it away. On the third day of the event, a quiet old lady that had sat quietly in the corner with her grandson the entire time approached us after the rude man and his guests that day had been extremely disrespectful to myself and my friend. She was a firecracker. She told us that she had been listening to the treatment we had endured over the previous couple of days and had negotiated to buy the company the rude man worked for and was working to relieve him of the position that he held. I don’t know if this ever came to pass but she made the two of us smile for the rest of the week after that. She was the hero we never deserved. I can’t remember most of what she said but one particular thing did stick in my mind, the first thing she said to us after the man had left ‘I could buy and sell every single person in this room, so I have.’ Legend.”
She Acted Like Nothing Even Happened!
“In college, I dated a college student who was the daughter of the Sony America Division president. We are at some fancy restaurant in Boston. We are eating our dinner when a dude seated next to us gets on one knee and proposes to his girlfriend. The girl said yes. My girlfriend congratulates them and as an engagement gift writes them a check for $10,000.
A couple weeks later I ask her if that check was ever cashed. She literally forgot about it. A quick phone call to her financial manager (yes, she had one of those) confirmed it was indeed cashed. She shrugged it off like it was no big deal and proceeded along like nothing happened.”
“I’m three years into Sous chef at a private resort in Upstate New York. Most of our guests are returning from generations before them. Wealthy. Very wealthy. We get some Congressmen and actors getting away from the daily mess. But mostly families that are crazy rich, and four generations deep into annual visits. Insane the number of requests. But – one that stands out; a 60 something-year-old woman crying as loud as she can because we didn’t have the cookies she wanted. Guys, you would’ve thought she was just told someone died. Made a huge scene in the dining room. Her husband has 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 store bought cookies because we do not have time for that mess. WE DID NOT TELL HER THEY WERE STORE BOUGHT. She was happy by the end of the night. Yay? Fast forward to dinner the next night. Same thing. ‘Where’re my cookies?’ We gave her the same store-bought cookies. Same package. ‘These aren’t the same. The Baker used too much butter this time.’ Next night? ‘Oh, these are much better’ LADY ITS THE SAME PACKAGE!! She comes every year. We all know ahead what week the ‘cookie lady’ is going to be staying with us so we can get her terrible grocery store cookies.”
Mrs. Richladypants Was Too Much For His Career
“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.’
I ended up turning down a job there, thankfully so because apparently, she wasn’t the only guest of her type there.”
Generous Thanks To Our Servicemen And Women
“We held an annual ball at a local marina hotel restaurant/bar for service members. 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 fifteen years, 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 abandoned uniform 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.
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, completely covered that night. It was glorious.”
It Must Be Boring To Live In A Family Like That
“I worked in an upper-middle chain hotel in Freiburg, Germany last summer.
Now, Freiburg is Germany’s warmest city and an absolutely gorgeous place, so apparently, a Saudi Arabian travel guide highly recommended the city. Cue the onslaught of black Mercedes mini-busses filled with Saudi Arabian tourists.
One day, a thief decides to chill near our bar and scope out potential targets in the breakfast room. It didn’t take him long; an elderly Saudi Arabian woman joins her distracted family at a table, plops down a backpack, and heads off to the bathroom. The thief slinks over there (very awkwardly), slowly extends a hand, retrieves the backpack, and bounces. Ten minutes later, the entire family is at my desk screaming. Apparently, the bag contained 5000 EUR and about 10 tablets/smartphones.
So we call the police and go through the whole ordeal of searching the premises, burning the CCTV video to DVD for a detective, and so on. When it’s all said and done, the patriarch of the family approaches my desk again, and hits me with:
‘Hey. Could you order me a taxi to Stuttgart? We want to go shopping.’
Stuttgart is a multi-hour drive away. A first-class train ticket there for his whole family would have been cheaper than a taxi. But he insisted and ended up paying over 900 euros for a taxi. I thought he was in shock after the theft and unable to make clear decisions; I really tried to reason with him, but he wanted to take his wife and mom shopping there.
I saw him the next day, and he casually informed me that he hated Stuttgart and is never going back. When I inquired why he said he spent around 10000 euros on jewelry and gifts at the mall but had a very difficult time getting a taxi ride back to Freiburg. Go figure, I thought to myself. But apparently, he found a willing driver and shelled out another 1k for the ride home.”
High Class And Highly Complicated
“I worked in a high-class restaurant in a nice hotel (for my town anyway) for a few years. We had a couple come in with their lapdog religiously every Tuesday evening for dinner. Due to 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. Also, they saw the menu as more of a ‘mix and match’ situation, rather than a thought out, cohesive guide to ordering, with each component of each dish tailored to complement everything else on the plate. They chose whatever sides and sauces on the menu struck their fancy, and paired them with their chosen protein, and they often ordered two different mix and match entrees each, plus a starter – They ALWAYS ordered the cheese and cracker board, no crackers, sub gluten-free bread (double toasted).
The lady sent the first round of bread back every time. We could’ve sent the first round out burnt, and she would’ve sent it back to be toasted more or re-sent the bread she had just sent back without doing anything to it and it would be ‘just divine’ the second time around. They subbed all 4 or 5 of the local, artisan cheeses for Brie, which wasn’t even one of the cheeses that came on the board, to begin with. We started keeping a wheel on hand specifically for them. Oh, and a ‘lightly seasoned’, grilled chicken for the dog. They were polite and delightfully odd (plus they tipped through the nose) so once we got used to most of their quirks, we were more entertained than annoyed, and enjoyed their weekly visit.”
They Thought They Were A Big Deal
“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? etc. But of course, she couldn’t name names. I rolled my eyes, told her whatever they need 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 smug-looking 20-somethings. 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 pricks.
Shock of shocks, they treated our staff horribly and tipped even worse. We did try to add 18% gratuity (standard for the group size) but the party threw a massive fit about that, complained about the service (which I’m sure was fine, it was a well-known place) and refused to pay it, so the manager took it off so as not to create a bigger scene. Left the server in tears. I think everyone just wanted to get them out by that point.
Will never know who that person thought they were.”