The only problem with eating the rich? They’re way too toxic! From spoiled brats to entitled adults and everything in between, these people had the misfortune of coming across the worst jerks money can buy.
1. Bottle Service
I was opening a bottle for this table when I started getting chest pains. I was scared because the last time that happened I had a seizure. The pain hit so quickly that I almost dropped the bottle, so I put the bottle down on the table. One lady said: “Honey are you okay?” because it was clear something was wrong. The man who ordered the bottle said “We aren’t paying $50 a person for you to die here.”
After a couple of seconds—which felt like it lasted forever—the pain gradually went away and I apologized and explained what happened to me the last time. Then the man replied with the cruelest words: “At least you didn’t drop the bottle—it costs more than your life.” Tears started to well up in my eyes as I poured their wine. I never went back to that table.
The lady who asked if I was okay came up to me later and apologized for the man and gave me a $100 tip. But still I remember feeling completely worthless at that moment. The bottle cost $300.
2. Beached Corvette
Worked at a fast food place across the street from a very big university for $8.25 an hour for years. Worst one I ever saw was a pretty little white blond girl (they are nigh infinite around here) literally in the middle of our restaurant on a cell phone. I noticed she was getting redder and redder in the face and being super animated.
Over the course of a few minutes as she was standing in line, and then all of a sudden she is screaming at the top of her lungs so loud her face was strawberry red… “I need my $500 EARLY this week! I talked to that idiot you married about it already! Tell your guy to get that money in there NOW!!! I have a party I need to go to TONIGHT!!!”
She whirls around at the two guys in line in front of her and demands she be allowed to cut them because, “Apparently, I’m in a freaking hurry to get to the bank!” They deny her, which sends her into another rage. “Screw this whole BS university! I freaking hate it! I wish I would have gone to New York!” She jumps into easily a $30,000 Corvette and shoves it into reverse—then instant karma hit her like a ton of bricks.
She pulls out into the aisle of cars and then puts it in drive, loses control of the car, and hops a divider, basically beaching her car with its super lower clearance. The back wheels get traction just enough for the car to suddenly lurch backward and the whole front bumper rips off and extends enough to detach from the body of the car, but not totally off of the car to let her go anywhere.
Gets out, starts slamming her fists into the hood. She is screaming so loud I can hear her through the thick glass that separates us from the outside parking lot—but it wasn’t over yet. Like CLOCKWORK a UPS truck hits a puddle next to her and freaking DRENCHES her with water from about her hip down to her legs. She was wearing a skirt.
She only partially moved herself away from the water and started screaming. I got off 15 minutes after her little episode but stayed at work for the next two hours watching her have a breakdown as the tow truck showed up to get her car off the median. What I can assume is a boyfriend picks her up in an equally expensive car with a towel in the front seat so she doesn’t mess up his interior.
The moment he got out of the car, she started screaming at him for making her wait almost an hour to come and get her and he just looks 100% defeated. I sat there with a cherry Fanta and watched it all from a window. I am sure daddy paid for it all but hey, it was the most entertaining thing I’d seen in a while.
3. Neat Freak
I worked as a valet for about a year at a really classy hotel. We routinely had Mercedes, BMWs, Range Rovers, football players candy colored cars, Porsches… Think of pretty much any kind of high end car and I must have driven one at some point. One time, a guy pulled up in a decent Mercedes, not anything super high dollar. He seemed cool at first, but then he did the rudest thing I have ever seen.
After I gave him the valet claim ticket, he casually went to his back seat and retrieved a newspaper. I was still holding the driver’s door open for me and he started disassembling the newspaper. Once he had 4-5 single sheets of newspaper, he began setting the newspaper on his driver’s seat, as if to protect it from my apparently dirty self. He didn’t even have to say anything, and it was still the rudest insult I had ever received
4. Where There’s a Will, There’s a Brat
He was 25 years old when I knew him. His father owned oilfields. He had a credit card that he used for anything and everything, which his parents paid the balance on every month. He never even kept track of what was charged on it, just bought whatever caught his fancy. He openly and shamelessly admitted that he had offered his college professor money to give him a passing grade.
One day, he was cranky about something and said something I will never forget for as long as I live. He genuinely meant it too. He said, “I wish my parents would just die, so I could have their money. Why should I have to wait?”
I worked in the VIP area of a now-defunct stadium. I was in high school and was working a summer job washing dishes. We served various VIP staff including the stadium owner. The owner was actually okay. He even thanked us one time, which was more than we usually got from our guests. His relatives, however were another story…
One day we hear a shriek coming from one of the guests, it sounds like someone was being attacked. My boss, the head chef, runs out to see what just happened. Turns out there was some dressing on the handle of the label. And one of the owner’s relatives was shrieking like a rat had just popped out of her food!
6. Daddy Warbucks Comes Back with a Vengeance
I worked as a bouncer at a high-end night club. The biggest boner of a rich kid, straight out of Malibu’s Most Wanted, gets a VIP booth and bottle service. Racks up a massive bill trying to act like a baller. His credit card gets denied, and he has to call his dad to come down at 1:30 am because he can’t order any more bottles. His dad comes down in his pajamas. Obviously ashamed and furious at this brat of a kid.
Ends up embarrassing the heck out of his kid in front of his whole group of friends. He takes the kid’s keys and is about to leave when his kid makes some trashy comment and goes back in the club. The dad’s about to walk away after he apologizes for his son, when we offer to drag him out the rough way. He smiles and accepts. That kid hit every door and step on the way out.
Not the best story but was one of the most satisfying experiences working at that club.
7. 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.
8. More Than They Bargained For
There was a kid in my fraternity whose parents were literally billionaires. We actually had a couple of them, but this kid was just dumb rich. For making the Dean’s List one semester, his parents let him get any car he wanted under $100,000. I am not making this up. Well, the kid’s response to this was incredibly disturbing.
He got enraged because the customized package he wanted on his Jaguar F Type made it over $100,000 and his parents wouldn’t let him have it. At first. After enough protest from this brat, his parents said “fine.” At least I got to drive it sometimes though; it was a sick car. For what it’s worth, the Dean’s List is NOT easy to get on at my school. Still, this kid still doesn’t realize how lucky he is.
9. Free Childcare
My friend graduated college with an engineering degree and had a great job making tons of money, but then quit because a guy whistled at her. After that, she worked as a waitress for 20 hours a week and got pregnant. Her parents bought her a house with the expectation that she would pay to rent. This did not go to plan.
She stayed at this house (which is beautiful, by the way) for six months and never paid once. Meanwhile, her baby daddy lost his job and spent the rest of his days playing video games. She got into an argument with her parents and moved in with her boyfriend’s parents instead. She then got into an argument with them and tried to move back home.
Here’s the crazy part—her parents let her…rent-free, utilities paid for, and they now watch her baby too.
10. 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.
When I was working at a public library, we had a few local celebrities come in from time to time. Most of them were nice, but one had a real stick up his butt. He would whine about having to stand in line, about late fees, and about everything else. We would just say, “Sorry, those are the rules,” or, “Thank you for being patient,” even though he wasn’t.
One day, he and I were apparently both having a bad day, and when I told him there was a limit on how many DVDs or video games he could check out at a time, he slammed his hands on the desk and raged, “Do you know who I am?!” This is a fully grown man, mind, and I was a little college student who barely looked old enough to drive—so I finally just snapped.
I was sick of his low-key teasing, so I looked at him and said, “Yes, I do, Mr. X, and the rules still apply to you. Which of these would you like me to put back?” He was stunned. I don’t think anyone had ever actually told him that the rules for everyone else did in fact apply to him as well. He was a little nicer after that. Not a lot nicer, but still.
12. Her Ego Puts Her Over Carrying Capacity
There was this incident I heard about a couple of years back about a local socialite, who married into one of the richest and most powerful families here. The story goes that she was at a bank’s main office to meet with the CEO. Instead of taking the elevator like a regular person, she had her bodyguards remove all the people inside the elevator so that she could go up alone without people bothering her.
She said something along the lines of, “Get out of my elevator.” Funny thing is, one of the people she had forced out the elevator was the bank owner’s wife, who decided to take another elevator with the rest of the people who were forced out. The owner’s wife got her sweet revenge. Once the socialite got to the office, the bank owner’s wife was already there and promptly told her to “get out of her building.”
13. 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 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.
14. Keys To The Jet
About 25 years ago, I had a summer job at a very posh country club. It had a six-figure joining fee plus five-figure continuing membership dues, and that got you nothing but the privilege of paying top dollar for rounds, food, etc. I was a porter some of the time, as we had cottages on club grounds for members to stay and make a weekend of it.
One of my duties was driving members to and from airports—usually, they were private airports for private jets. One time, I was driving these two guys to the airport and one of them started complaining. It seemed as though he and his wife were always fighting over who got the jet every weekend, and where they wanted to go.
Well, the other one replied, “My third jet is actually just gathering dust right now since my son went to college. Wanna take it off my hands?” They shook on it right there in the van.
15. Tying The Knot, Cutting The Cord
My college roommate (and former best friend) grew up spoiled as an only child. She lived in this huge five-bedroom house for just the three of them, had a fancy car to play with that had all the bells and whistles, as well as daddy’s credit card. When I got engaged, I asked her to be my maid of honor. She told me no—and her reason chilled me to the bone.
She said couldn’t approve of my marriage because my fiancé didn’t have a bachelor’s degree, so she was just certain that we couldn’t be happy. Eight years and two kids later…I’m still not rich, but very happy. I still have my hot karate instructor husband who turned out to be a much better deal than a sugar daddy.
Obviously, I had plenty of other issues that came up over the years with her, but this was just icing on the cake.
16. Any Way You Want It
This is a girl I have known for most of my life. Her parents treat her like she is the Queen of England or something. Growing up, if there was a new toy out that she wanted, her parents would buy her five (in each color, if possible) because she would often break her toys. She also had three bedrooms; one of which was big enough to be a studio apartment alone. But hold onto your hats.
Where did she sleep? Her parents’ bedroom. If she wanted to go somewhere, like Disney World, her parents dropped everything they were doing to start planning that vacation. When she started driving, she had three new cars in eight months. Not because she crashed them or they broke down, but because she just had to have the newest model.
She has never had a job. Her parents pay for everything. In school, she had a “tutor.” I say that in quotes because the tutor basically just did her homework for her. I’m surprised she can even read and write, honestly. Though, reading her Facebook statuses, it looks like she can’t write much better than my nine-year-old. It gets darker than this, too.
The worst part was that if she didn’t like someone, she had her parents do their best to ruin that person’s life. Honestly. She got her seventh-grade teacher fired, claiming he was being inappropriate with her. He wasn’t; he was never even in a room with her alone. He was a kind, old man, but he didn’t put up with her not doing her homework.
He failed her in a few subjects…that was it. He was never charged or got into real trouble from it, but the school did force him into retirement because they were scared.
17. Out-Evil-ing the Genius
I was out at a farm with my cousins for a party. It was more like an afternoon barbecue with all the parents sat talking and cooking while the kids ran around playing. Usual lazy afternoon in Africa. So anyway, I was 16 at the time, making me the oldest of the kids. I will admit that I was a back of the bus/too cool for school type of cringy teenager and was practicing my casual aloofness.
Now, there was this German couple there with this absolute monster child (5) who made it his mission to terrorize all the other kids. The parents of little Adolph sat beaming with delight watching their little ray of sunshine playing with the other kids. Eventually, it became apparent that they were going to do nothing about it.
My parents told me to keep my cool and just ignore him. I did because I didn’t want to put my parents in an awkward situation. At some point in the afternoon the kid found one of those plastic toddler toys, you know the ones where they can sit on it and push themselves around but it also has a handle at the back that toddlers can use like a walker.
So, he finds this toy and is running around this lawn full-speed ramming all the other kids. Now, I did tell him nicely that it was not good to hurt the other little boys and girls, but he clean ignored me and carried on with his game, giggling and chasing the other kids. He also decided that I was now fair game and I got rammed in the ankles and Achilles tendon a few times.
I’m fuming. His parents were watching and laughing the whole time. So, I come up with a devious plan to ruin their day in the best way possible. I position myself in front of this small ditch (only about 1/4 inch deep and full of tall grass) and pull out my phone pretending to read messages. I was making myself an easy target for the little brat.
He comes charging up behind me aiming for my heels again. The front wheels go into the little ditch, stopping the walker. The kid was pushing it so fast that his momentum carried him right over the handlebars, right over the push toy and past me. He faceplants in the dirt going full scorpion. There was no blood but he lay there and screamed as if he’d been shanked.
The best part was that the parents watched the whole thing take place and they and the other parents never suspected that I stood in that exact spot for that exact reason. His parents were kind of ticked that the kid hurt himself while I was watching the kids but they couldn’t say anything so they just kept the boy close the rest of the day.
18. The Widow’s Windfall from Grace
My Pops (grandfather) handled all the finances for him and my Nana (grandmother), so she never did the shopping or paid any bills. Her net worth now as a widow isn’t shy of £1m. When Pops died, she bought herself a brand-new car that was tailored to her disabilities, because again, Pops always did the driving. Her car was around £16k.
This was her first experience of buying a vehicle and thus thought this was the standard price for ANY CAR. I bought myself a new car a few months later. It was the same model as hers but a few years older and had previous owners. All my other cars had come in under £600, and this new car was £5k and I took it out on finance, which was a huge deal for me.
When she asked how much my car was, she was terrified that I’d bought a rundown POS car, and that there must be something horrendously wrong with it. We had to explain the value of cars to her and why mine was £10k less than hers. Flash forward to this year, my broke brother’s deathtrap car pretty much exploded, so she took him to buy a new one.
He’d seen a pretty good car for just under £1k and figured that’s what he could afford to pay back. Before he mentions it, she drags him to the dealership and buys an approved used car (same model and year as mine) at £3k and can’t believe her luck at how cheap it was, and gifts it to him because it was so cheap. Brother is speechless and very grateful.
This is the same woman who had an absolute meltdown because her Ambrosia custard pots had risen in price by 20p, and she was now (very seriously) concerned that her continued purchase of them would bankrupt her.
19. Tax Pains
I worked a summer camp for a few years when I was young and the trees were greener than the trees you get these days, and the grass was more potent. My final year, I was the assistant manager, I forget what the title was (Events coordinator or something stupid like that). The camp had campers for ten days, then four days off.
Pay was given at the end of the ten days, except your first pay also included the four days of training before the first campers came. I had nothing to do with hiring, but I figured Princess Peach Pitt was going to be a problem when it came to the first day of training. She was about as useful as a handsaw on a space shuttle and as bright as a candle with no wick.
When she found out that counselors had to do some light cleaning after campers ate, she nearly had a conniption fit. I found out that she got the job because mom and dad were good friends of the CEO of the organization that ran the camp, and they wanted her to have some “real world” experience before she went off to university.
Well, we made it work. She got easy to deal with campers, had the most experienced partner, and the only downside for her was the Events Coordinator kept a close eye on her to make sure she did her fair share of the work. On the last day of camp, the campers left and the head of the camp had to leave early, so had me distribute the pay envelopes.
So, I do so (staff of 30, took no time) then went to the office to finish off the paperwork. There’s a knock at the door. It’s Princess Peach Pitt. “My pay is wrong.” She says. “I’m sorry to hear that, unfortunately (head) had to leave early, so it’s something we’ll make sure is corrected on the next cheque. What is the problem?” She replied, “It’s short by, like, $300! I don’t think I got paid for the training.”
“What?!” I exclaim. She says, “I’m supposed to make $9/hr at 80 hours plus four days training, which comes to over $1000. This cheque is for less than $700. I have plans for this money, and if I don’t get it, I will sue.” I wanted to say, “Welcome to the real world.” I wanted to say, “Oh my sweet summer child, why couldn’t you have been taken by the faeries, as this world isn’t for you.”
What I did say was, “Okay, so after income taxes are deducted, that sounds about right.” What followed was a declaration that we had no right to take taxes from her. I suggested she should write to the prime minister and perhaps talk to her parents about her recourse from here, but there was nothing I could do to help her. I did hope she wouldn’t return in a fit of pique, but she did come back and worked the rest of the summer. And she never sued the organization.
20. Clean Shirt Club
One of my favorite moments in all TV history came on a show where they had the adult children of billionaires working as cattle hands on an actual cattle drive under the supervision of one real cowboy. Fed up with being dirty all the time, one of the guys proposed to the cowboy that he should be able to have clean shirts delivered to him as he made his way through 100s of miles of plains, herding cattle.
The cowboy was obviously incredulous. “Let me get this straight—you want to hire someone to bring you a dry cleaned shirt, out here, in the middle of nowhere?” In a way that I can only categorize as utterly clueless, the kid responded, “It could be fluff and fold!” As though the manner in which the shirts were cleaned was the issue.
This was probably 10 years ago or more and I can’t go into a dry cleaner to this day without chuckling to myself at how unbelievably out of touch with reality this kid was.
21. She Could Do the Time, So She Did the Crime
On the hill from Hampstead tube station, some Joan Collins 1980s clone of a woman parked her Range Rover outside a shop on a double yellow line (no parking on that road) with her hazard lights flashing. She was coming out of the shop carrying her frou-frou little paper bags as a traffic warden was fixing the parking ticket to her window. Her reaction was priceless.
She snatched it from the windscreen and said in a posh but aggressive voice, “I don’t care. I can freaking afford it.” Threw the flapping paperwork into the vehicle and roared off down the hill. To most of us, parking meters and Do Not Park signs and road paint are parts of society with a financial penalty to keep the system going.
For this woman, it was like having a park-where-you-like system that occasionally had a fee that made her whiny and wasted the time it took to write out the cheque and post it for the fine.
22. What Are Friends For?
Let me tell you about a fellow I’ve known for almost 30 years, who has yet to grow up. We’ll call him “Brad.” Brad is from a very wealthy family, courtesy of his dad’s government work. For some reason, his parents fell in love with the small town I’m from and moved the family from the big city to our flyspeck, nowhere town.
When they first moved, they had Brad and his brother in a private school, but they eventually moved them to a public school. A mutual friend introduced me to him and he ended up in a lot of my classes. We bonded together over comic books and RPGs. Brad’s parents were incredibly free with their money toward their sons.
There were literally entire rooms of their house devoted to everything the kids bought. In high school, I worked out that Brad was getting around $500 a month to buy comics and video games with. After high school, his parents paid for the entirety of his college education. During his four years of college, he had a job for one day, which his father got him.
After college, he moved back to the area, his boyfriend in tow. His family supported both of them in an apartment for several months before he finally landed a job. I don’t know whether his father helped him get the job, but the fact that he bragged about sleeping at his desk regularly makes me suspect he helped him find employment. Then things changed for the worse.
His brother, who was always the favored son, got spoiled even further. They gave him a house, among other things, and the gravy train Brad once had begun to dry up. As a result, Brad turned very bad. You see, in Brad’s mind, since his parents are no longer subsidizing his life, it’s up to the rest of the world to bend over backward for him.
You’re out to eat with him and you have leftovers? You should give them all to him. You’ve got a new computer game or e-format book he wants? You should make him a copy. You’re playing an RPG? You should memorize exactly how his character works and tell him what he can do each round so he can beat the game without really trying.
You have a family emergency and can’t make it to an event he’s at? You should ignore your flesh and blood and come out with him anyway. For more years than I can remember, anytime anyone refused one of his self-serving demands, he would get enraged, sometimes to the point of throwing things or leaving in a huff.
Without fail, he would shout “SCREW YOU!” at the top of his lungs, at a decibel level you would never expect from a man his size. Eventually, we all got tired of his behavior, and one night, as he began a tantrum, everyone present shouted: “SCREW YOU!” at him in perfect unison, even mimicking the gestures he made.
He mellowed after that. I cut him out of my life for several years, for reasons related to his boyfriend. He’s been reappearing in my circle of friends for the last year, though he frequently ghosts them. I understand he’s out with his parents whenever he does this, and I suspect he’s hoping to become the favorite son again.
23. A Mother’s Love
During one of my substitute teaching assignments, I had the pleasure of meeting the most spoiled teenager I had ever encountered before. Conrad was spoiled in the way only children of rich divorced parents can be. Conrad was spoiled because his parents thought that material goods and money would buy his affection.
On the first day of this particular sub-job, Conrad informed me he didn’t have to do his work since he would just get his father to pay the teacher “a buttload of money” and he would get an A. I stated I didn’t care what he did as long as he did not disturb his classmates, and then he wrote his comments in my sub notes.
He was placated for the day and dinked around on his cell phone until the period ended. The second day really showed Conrad’s true colors. He was “working” with a group of his friends, but he spent the entire time continuously talking about how much he hated his mom because she bought him a used 2013 Ford Focus for his 16th birthday instead of a brand-new BMW that he wanted.
I told him that I would love it if my parents gifted me any vehicle, to which he commented, “Of course you would. You’re a teacher and poor.” I told him to get back to work and if I caught him off-task again, he would need to work alone. He was fine after that. On the third and final day of my assignment, Conrad was in an absolute tizzy about something his mother had done.
Probably the BMW thing. I didn’t know or care…until I heard the horrific words coming out of his mouth. he kept commenting on how he was going to sabotage his mother’s plane so that “the witch would fall out of the sky and die.” I told him to rein in those comments as they were not appropriate for school. I left him with his group to continue their work from the previous day.
Approximately five minutes later, I heard nervous laughter coming from Conrad’s group. He had his phone out and was showing the group something on it. I walked over and asked to see what was causing such a fuss. Conrad, the idiot, showed me his Snapchat story, which consisted of a picture he took of his mother with an emoji gun pointed at her head.
I sent him to the office to talk to the school social worker and the school resource officer. All because this kid didn’t get a BMW.
24. Lost My Drive
Went on a double date with my boyfriend, his friend, and his friend’s date. The whole evening, she was rude, snobby, and overall a demanding person who felt entitled to whatever she wanted. She was rude to the waitstaff and suggested we tip them nothing for refusing to refund her order after she ate the whole thing, and complained about everything.
On the car ride back, she started driving, then halfway through the drive, announced she didn’t want to drive anymore. The rest of us had been drinking, so we all refused to take over. She said, “Fine, but I’m not driving either,” let go of the steering wheel, and slammed on the brakes. We got rear-ended, and it was her car, so no cost to the rest of us, but it was instant karma for her behavior and attitude.
For a couple of years in high school, I went to this super expensive American private school in Switzerland. The company my dad worked for paid for almost all the tuition, so it was an amazing opportunity for me. Most of the kids in this school were either State Department or from American families living in Saudi Arabia (the Saudi government provided ex-pat kids with school up until 10th grade, so you had to go to a school abroad to finish HS).
There were, however, a few Saudi kids that were there, mostly so that they would be able to speak flawless English to help out their future careers. One of these kids, who I will call The Prince, was somewhere in the line of Saudi succession, but honestly, he was like 1,455th in line for the throne. Not a real contender for King, but his family was rich. Like, rich in a way that most of us can’t even imagine.
This school had some rules, like you couldn’t have a car as a student, even if you were old enough to get a license in Switzerland. This rule was a real buzzkill for The Prince, but he made it through the year somehow. Over the summer after his Junior year, he drove back to the school from Geneva in his Lambo, probably just because he could do it outside the school year.
On his way up the mountain (the road is like an endless series of hairpin turns) he managed to flip his Lambo into a vineyard while trying to navigate one of those tuns. I’m guessing a Lambo has a lot of power, and he took it way too hard. His parents, furious at what he had done, decided to punish him by replacing his Lamborghini with a Porsche.
Of course, The Prince was SOOOO angry. He complained about it bitterly when the school year started up again. The rest of us kind of just looked at each other in amazement. Same planet, different worlds I guess.
26. But Daddy!
Freshman year of college. The guy across the hall from me is a spoiled rich kid from a big southern city. Old money clearly coming out his butt. A couple of weeks into the second semester he and a buddy found a checkbook on the sidewalk. Stupid morons decided to write themselves a check and cash it in the bank that the account is in.
The teller immediately called the authorities and they both got detained. We talked the night he got detained and he laughed and said his dad would “take care of it” and everything would be fine. That weekend we met his dad as they moved everything out of the dorms since his dumb butt got expelled. Guess daddy didn’t take care of it.
27. A Game of Telephone
I work in local theater, and we have a lot of rude, awful women from the nearby ballet schools come through our venue; they’re generally the mothers of the dancers so you know, those awful controlling rich dance moms you see on TV. Once, this woman rang up wanting seats to an almost sold-out ballet performance that had been on sale for four months the day before the show. It did not go well.
She did nothing but scream at me for five minutes because she left buying them too late, whined about how she shouldn’t have to pay to see her kids, whined that we should get a bigger venue, then put me on hold while she rang three of her relatives to see if they wanted seats too. She was positively horrific to me.
The seats I was about to sell her were the only ones in the theater left, and they were actually good seats. While I’m on hold, a grandma of one of the ballerinas comes to the desk and asks nicely if we have any seats left, as she’d been in hospital and couldn’t buy them earlier. She said she’d understand if we were booked out.
This awful woman still has me on hold, so I put the phone down and sold this old lady the last seats for the show, then gave her an invite to our next year’s dance season so she’d know exactly when all the important dates were coming. She thanked me over and over, and she’s now one of our regulars and brings her grandkids to our shows. Meanwhile, this other lady…
Two minutes after the old lady leaves, the witch on the other end finally takes me off hold and says she wants the remaining seats that we have left, I tell her “Sorry, we’ve just sold out while you had me on hold I’m afraid, better luck next year, anything else I can help you with?” She was choking with rage on the other end of the phone, it was fantastic.
28. Too Big To Fail
I worked at a private school in the UK this past year and I have a few examples of kids having no idea they were spoiled, which just made it worse. One day, this 16-year-old old came into school complaining about how unfair it was that his dad grounded him….for crashing their plane. But that’s not even the worst part.
I asked him how bad it was and he said, “It was only £40,000 worth of damage,” which apparently his dad could afford, so he didn’t know what the problem was. My jaw dropped. Another 16-year-old once asked me what I was doing for summer break. I told him I was mainly going to be working. He COULD NOT wrap his head around why I wasn’t traveling, going on holiday, etc., then went on about how he’d spend his summer at his private lake. But nothing beats my third student.
On his birthday, one of the 18-year-old old students received a chain of hotels. A fully operating, five-star chain that would all be officially owned under his name. The nerve of this kid to complain that it wasn’t what he wanted…it made me really resent working there for a while.
29. A Glass Half Empty Kind Of Girl
My ex-girlfriend. She grew up in a really fancy town in Illinois called Evansville. One day, we went to a really great sushi place, and she complained that the rice was too chewy. She accused them, the Japanese owners who had lived in Okinawa for 30 years, of not knowing what authentic sushi tasted like. The audacity…
When I bought a new car, she constantly complained that the seats weren’t soft enough. Witch, those seats were like giant pillows! Another time, we attended a friend’s small party on a sports yacht in Miami. She complained of the fish smell. We were on a freaking yacht. On the ocean. It was going to smell like fish. I had to end things after that.
30. Weekend Trips To Bali
I went to a very expensive private school. I had a lot of scholarships so I wouldn’t have to pay the $52,000 a year they were asking for. At the time they had a very lax acceptance policy but were considered a great school, which had the interesting result of attracting very rich kids who weren’t interested in the school for its academics but more for its parties and nightlife.
In my dorm during freshman year, there was a girl who supposedly is a descendant of the Versace family of some sort. After seeing the money she’d blow nonchalantly, I was inclined to believe it. Almost every weekend there’d be a knock on our door as she ran through the halls asking who was coming with her on her trip this weekend.
She didn’t mean her trip to the grocery store or even a trip home. She meant whatever trip she was planning around the world that weekend. Sometimes it was Paris, others were Australia, Bali, wherever her little heart desired. She’d fly out to these exotic places for weekends, not three-day weekends, not holiday breaks, just your average Friday/Saturday/Sunday.
She would be gobsmacked and sometimes insulted when after a moment of stunned silence, you tell her that you couldn’t possibly go with her to Paris for three days let alone afford a last-minute ticket to Paris. She just couldn’t comprehend that normal people couldn’t afford those things. She also “lived in the dorms” because she was a freshman, and you couldn’t live off-campus as a freshman.
But the dorm was just a facade. She actually lived off-campus in what I would later find out to be a $4,000 a month apartment by herself with a house cleaner who’d come every day. She was the most detached-from-reality person I’ve ever met. And of course, she was drop-dead gorgeous. She’ll probably never experience a “hard time” in her entire life, or have to work a single day.
31. Mind Games
Back when I was a server, there was a woman with a group of friends at one of my tables who asked for a can of Coke. When I brought their drinks and gave the woman her Coke, she looked at me and said, in that typical rich-girl voice,”Excuse me, honey? I asked for Fanta, not Coke.” I apologized, wrote it onto my notepad, and went back to get her a can of Fanta.
I brought the drink to her but again she turned to me and said: “I didn’t ask for Fanta, I asked for Cream Soda.” By this time, I was getting a bit annoyed, but I went back and got her a Cream Soda anyway. Sure enough, when I returned to her table, she did the same thing again. “I asked for Sprite. Should I call the manager?” Oh, honey. She should have stopped testing me when she had the chance.
So, for the last time, I smiled and I went back to the kitchen and packed cans of Coke, Cream Soda, Fanta, Sprite, Pepsi and Sparberry Soda, into a small plastic box and took it all to her and said: “Here you go, miss, take your pick.” She looked offended and almost made a scene. She started lecturing me about how I’m incapable of getting the simplest order right and that she wants to talk to the restaurant’s manager.
I told her that I can call him, and that I’ll show him all the soda types I wrote on my notepad that she asked for, and we can get his opinion on the matter. She turned and took her Sprite out of the plastic box and said “Just leave it.” None of them gave me any issues after that!
I was a sous-chef at a fancy country club and it was 10 minutes before we opened for the Easter buffet. Needless to say, it was going to be a very busy day. I was walking through the dining room and checking all the final details when suddenly a little girl of about two years old ran into the room. She had escaped from her mom who was at the front desk.
She comes to a stop about six feet in front of us and looks up with her eyes wide. I must have been quite a sight, I was wearing my tall white hat and white apron down to my toes. Her mom appears in a heartbeat, turns her daughter by the shoulder, and whisks her away saying: “Don’t talk to them, that’s the help, dear.”
33. Thanks But No Thanks
I worked for the University Mail Services in college, it was mostly just sorting mail but I occasionally helped out with deliveries and pickups on campus. One day I was running the route and picking up mail from one of the admin offices. There was a FedEx package to pick up, and for those, I had to sign the paperwork, note the time, and leave the carbon copy.
I had left my pen in the van, so I asked a couple who were passing by if they had a pen I could borrow for a second. They both looked at me like I’d asked to take his Ferrari for a spin. The guy looked down at his pen and then up at me before handing me the pen in the most condescending manner I’ve ever seen. Yes, he managed to make the act of handing me a pen condescending.
Then the lady said: “You should ask your boss for a raise so you can afford your own pen.”
34. Truck, Meet Face
When I was in high school there was this horribly bratty rich kid who loved to pick on others, push people around, and play the “Do you know who my dad is?” card a lot. Let’s call him Todd. I hated this kid, all through school. Final year of high school, I’d had a bad day one day, and it obviously showed. Todd sees me walking in the hall.
He makes some snide remark about my shirt. I promptly tell him to shove it, as I am not in the mood. He walks over to me while I am at my locker and slams my locker door, then shoves me. I recall that he said something else but I honestly don’t remember what it was. I just remember that I saw red, and couldn’t control what happened next. I drove my fist into his nose like a truck.
I stomped away all teenage and angsty. Got called to the office the next day. Todd is sitting there with his father and the principal. I knew I was screwed. The principal shows us all the security camera footage of what went down. I am assuming an expulsion is coming my way, when Todd’s father puts his hand on my shoulder and smiles.
He tells Todd to say thank you, and we both look at him dumbfounded. “Why would I thank him? He broke my nose!” says Todd. His father responds with, “Because if I had been there, and seen you act like that, I’d have ended you.” He stood up and left and I was excused to return to class. Todd never bothered me again.
35. Freaky Hobbies
I drove my boss’ friends around so they could meet up and swing. Sometimes, they’d rent out space by a local lake and sometimes it’d be at a “normal” upper-middle-class looking home. Other times, it’d be a home where “floor-to-ceiling glass windows” that went 30 feet in the air and among the top residential mansions.
90% of the driving around was to either pick up people, drop people off, or get drinks. One time, I ordered 100 taquitos from Whataburger the morning after. Nothing too weird about it, but people did prefer to be picked up and dropped off alone or with their +1. Carpooling was a big no-no. Nobody wore robes, but I did see some people had those masquerade ball masks.
People were always super talkative before being dropped off. Normally, they slept on the ride home. Few occasions that stuck out were a guy who had taken Viagra for the first time and told me all about it, and another guy who took his contacts out beforehand and always asked to borrow my contact solution and case.
If you hadn’t known they were swingers you’d think they were just hiring a designated driver to keep people from getting into trouble. Especially because none of them were particularly attractive, at least to me.
36. One Color Too Many
When rich people want to buy a Jaguar in the UK, they get assigned a special salesperson who is incredibly knowledgeable. They meet in a special fancy office, and special arrangements can be made. This was my friend Chris’ job. He had access to things that a normal Jaguar salesperson wouldn’t have, like ringing up the manager of the factory for special requests level of access.
Well, a Saudi prince wanted to buy this new Jaguar that had been released, so they met up and spent a full day customizing the Jaguar. The final price was something around 125k for the vehicle. Then came the decision for color. At the time the factory had 16 different color choices for this model. The prince asked if he could sleep on it as it was getting late and it was almost time for dinner.
Chris, of course, said yes and they set a time to meet the next morning. The next morning the Saudi prince said something like, “I figured out an acceptable solution to my color dilemma.” To this, Chris asked, “And what would that be?” The Saudi prince’s response was so outrageous—it’s unforgettable. He said, “I’ll order one of each color,” and Chris responded, “Oh, well, of course.”
They quoted the delivery time which was okay with the prince who then asked for his delivery options. On being told about ocean travel options, he asked about air cargo. Chris thought that they could do one or two by air and rest by boat. But the prince said, “No, I want all 16 vehicles loaded on a plane and flown to Saudi Arabia.”
So that’s the story of how 16 of the same Jaguar, in different colors, ended up being flown to Saudi Arabia. The total cost was around 2.5 million pounds.
There was a girl at my college with a big-shot oil daddy and she was the most insufferable human I’ve ever witnessed. She tried to brand herself as this super environmentalist hippy but used all of dad’s oil money for weekly trips across the country and the globe in private jets with insane wardrobes and fancy dinners.
I’ve never seen someone use money so frivolously while constantly on social media preaching about all the earth has given her or whatever. Seriously her Instagram posts are hilarious: “As I am soaked in the bright and glorious sun I am moved with gratitude. I give thanks to every part of my body, for warrioring me through life and for simply being. Thank you water you are life, may we protect you as you do for us. For the past week I have been deep in the shadow… what a darker tone this is compared to the rose gold clouds I normally drift in. I’ve leaned into the unknown, and I’ve chosen to embrace it all…. pains… grace…. peace… I am blissful.”
They just go on and on like that. Last I heard she “somehow” convinced the school to let her do a “special” graduation program in Hawaii and now her dad pays for her to live a “gypset” lifestyle which if I understand correctly is just flying all over the world on insane dime doing whatever you want?
38. Having Your Chocolate and Eating It Too
I worked at an independent chocolate shop that sold various flavors of truffles, brownies, and drinks. We also had non-dairy options, vegan options, and nut free options available. A woman demanded to speak to the manager because we did not have a “dairy free, nut free, sugar-free, vegan” option. Luckily, the owner totally owned her. He literally just laughed and said, “We do have one, it’s called water.”
I have never seen such entitled rage in my life!
39. The Fine Print
One of my favorite serving experiences was with a guy who had arranged a big family get-together at our restaurant. I was pretty efficient at waiting tables so they assigned me the whole party, it was probably a couple of dozen people. I was handling it well but the host was drunk by the time he got there and he was complaining that he didn’t already have a drink in his hand.
Then he noticed that I was wearing a pair of sunglasses on top of my head (it was an indoor/outdoor restaurant and I was also serving the outside areas). For the rest of their meal, every time I came to the table, he announced how stupid I looked to everyone. The others at the table got so embarrassed that they started to apologize on his behalf.
Our policy was to add a 20% gratuity on parties that big, so when the check came, my tip was already on it. There’s a line for an extra tip, which is clearly marked as “additional.” This guy grabs the check, looks at me, turns so I can see what he writes, as he draws the biggest “0” and struck a line right through the middle of it so hard he pierced the paper. He turns to me with the most satisfied grin and I just thank him and tell him to have a pleasant night.
The guy is too dense to realize he had already tipped me over $100. My boss and I had a great laugh about it.
40. Feeding Time
I have worked for some of the richest people in Maryland and the one thing that stands out more than others is this doctor I worked for in Montgomery County, one of the most affluent zip codes in America. This guy owned a lot of offices around the DC area, employing tons of employees and associate doctors, etc.
He was really wealthy. He had a place with a huge garage full of exorbitantly expensive cars like Ferraris, an art collection, a wine cellar—the works. I used to do IT work for his medical practice and managed all the servers, etc., and occasionally went to their house because I was the lead admin.
Once, I was working in his house and was walking around upstairs where the bedrooms were when I came across the most off-putting sight. What I see is that this guy was lying in bed being fed by an assistant. I mean, he was literally lying in the bed while someone, completely platonically, hand-fed him, and not something like grapes but a regular meal. It was strange, to say the least.
Imagine someone feeding you a full meal with things like a steak and spoons of soup, salad, etc. and you never use your hands. It was like an adult being fed like a baby. I’ve never seen anything like that before and that was what popped into my mind, like a dictator or something who demands to be treated like a literal king.
Keep in mind this was a man in his 50s who was in fine physical shape and didn’t need a caregiver. It was just pure opulence.
41. One For The Road
My dad works in shipping and has a lot of friends who have worked on super yachts. In the 90s, one of his mates got a call up to bring the yacht of a particular Australian media tycoon billionaire from Sydney to New York, with instructions to be anchored in a particular bay at an exact time with a lunch spread for 50 people ready.
So, they got there and set up the food. The guy never showed up. And the reason is so ridiculous—it makes me sick. Turns out that he was having a rich people party in a building overlooking the harbor and wanted to be able to point down and say, “That’s my boat.” He wanted the lunch prepared just in case he decided to take his rich friends down to his yacht, but he didn’t feel like it that day.
So, all the food got wasted and they sailed back to Australia without seeing the tycoon.
42. A Job Well Done
I used to do pool and spa maintenance in my 20s. During this time, I worked on one property with a mountainside, 10-bedroom, 14-bath mansion, with a saltwater pool, tennis courts, guest mansion, and a servants’ house that had four bedrooms and five baths. The property had so much more than this, but that wasn’t the craziest part.
For about two years, not a single person was ever there. The middle-aged, single woman that owned it lived in a city about four hours away and just didn’t come to the property, because she was so busy with work. A multi-multi-multi-million-dollar compound, just empty. All the time. Finally, after two years, I got a call from my boss on my day off.
He asked if I could go to the house to put some pool floats away. He apologized, because it was my day off, but said the owner would pay me $500 to go put them away. I was confused as to why there were even pool floats out anyway because nobody was ever there, but I figured who cares; $500 for 10 minutes.
I showed up at the house and the woman’s adult children were staying at the house with over 10 kids between them all, and they were having a massive pool party/cookout. I awkwardly walked up and said to one of the parents, “Sorry, it must have been a mistake, but I was told to come put pool floats away, but you’re obviously here so I’ll leave.”
But, instead, I got the weirdest response ever. The woman’s adult son said, “Oh, no, we’re getting ready to leave. You can take them.” Then he instructed the kids to push them towards me. I literally grabbed one inner tube float and four pool noodles, brought them 10 feet into the pool house, and put them away. I, confusedly, said they were all set and went to leave.
The son thanked me and handed me a folded mass of $20 bills. It was $400. I was expecting $500 from my boss for payment, but I figured that $400 cash was still overpayment for what I had done, so I didn’t mention it. The next day at work, my boss gave me another $1,000. I told him the son had already paid me $400, which was fine.
He said that the son told the woman what a great job I did, so she wanted to pay me $1000 instead of $500, and the $400 from yesterday was a tip from her son. For 10 minutes of work. She actually called my boss the next day to ask if she should reimburse me for gas since it was 15 minutes from my house. I told him that I was all set.
My family is pretty well-off, and we lived in a really snooty area. My dad grew up poor and got incredibly successful through hard work. He didn’t want his kids to be lazy, rich brats so he raised us to never be snobs. I worked as a dog walker in high school because he encouraged it (and because I just love dogs). One day I walked into one of my new client’s house and she commented: “I’m sure someone like you has never even been in such a big house!”
When I said I actually had she laughed and told me that “Walmart isn’t a house!” I was so baffled at her rudeness, I thought everyone who was well-off was as classy and humble like my father. Nope.
44. Peaceful Protest
When my brother was in school, he was horrifically teased for being autistic. Even worse, his aggressor was the most entitled little brat I’ve ever had the displeasure of meeting. His father paid for boxing practice, karate lessons, and other martial arts. This made him think that he was the best at anything physical and he used it against others.
My brother isn’t overly fond of sports, and prefers to read in the library. As the typical nerdy kid, he’s a prime target. One day when the jerk had cornered my brother up against a wall, my brother finally decided that he wasn’t just going to take it any more. But he strongly dislikes aggression, and thus would not be fighting back.
Instead, when the jerk tried to punch him…my brother ducked. Three broken fingers and a trip to the hospital later, the jerk’s father finds out what had been happening. All his extra classes and training were canceled, and he had all of his electronics and games sold. Also, if he wanted to have a car, he would have to work for every penny himself.
45. The Worst Victim
Back in high school (the 90s) this kid got a brand new Chevy Camaro. I had an old, beaten up 80s Pontiac Phoenix that had the straight six. It was by far not a racing car, but this tool was just looking to brag at what he got compared to the busted cars we got. About two days later, while we were waiting at a stoplight, this idiot pulls up alongside us and tries to race us.
He starts by revving it really loud and tries to do a burnout. Mind you the light was red, and the roads were not wet. So he managed to get a tiny burnout going, some smoke and whatnot. When his tires did catch traction, he went barreling into the intersection…and smashed into the car of the wife of one of the VERY FEW officers in my small city. Needless to say, that didn’t work out for him very well.
46. Jet Set for Misunderstanding
I was working in a fine dining restaurant and in one of our private rooms was the birthday party of a very well-known local rich guy. His wife was greeting people at the door, and my job was to stand next to her with a tray full of cocktails for her to offer people as they arrived. When there was a lull between arrivals, she started telling me a story that she thought was hilarious about the trials and tribulations of decorating their private jet.
I responded politely of course, but all the while I really just wanted to ask her if she honestly believed I could relate to anything that just came out of her mouth.
47. 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.
48. Someone Needs to Go Back to School and It Ain’t Us
I work landscaping and was working at a lady’s house, planting a tree and spraying the grass with pesticide. When we were packing up the truck, I heard her insult us. Little did she know, the joke was on her. She told her son to do well in school or he’ll end up working like us. Um, all but two of my coworkers on that job had at least bachelor’s degrees from major universities. I’m working on a master’s degree in conservation management right now. You actually need to be pretty smart and well trained to apply chemicals around houses.
49. Lead by Example
I used to work in this totally yuppie bowling alley. You might laugh at that, but an hour and a half of bowling and a pitcher is about $90 for two people. I went to check on a lane when a group was getting set up. They were a couple of well-dressed older white ladies with two Asian ~six-year-old girls, both in fancy little kimonos.
I greeted them warmly and asked, “Can I get y’all a pitcher of soda?” And one of the ladies gave me a dirty look and sneered: “You mean you all. I already worry about the girls growing up with an accent, and I don’t want them learning bad grammar as well.” I couldn’t believe it! She also made the girls practice their ‘bow’ for me and I was just generally weirded out by almost everything that happened.
50. Realtor Revelations
I work in high-end real estate so I’m in the homes of the affluent a lot. Once, I was in a home selling for over $10 million with two Bentleys in the garage. I overheard the homeowner talking to her friend in the next room. They said: “These new tax laws are destroying us in the middle class. We had to open another trust just to save more money this year.”
It’s insane that this woman really believes that she’s middle class. They continued: “The billionaires are pricing us millionaires out of the neighborhood.” She was referring to her gated community in Park City and I was apparently supposed to feel sorry for her.
51. Party People
I picked up a wedding party: a bride, bridesmaid, and the bride’s boyfriend who was paying for the wedding. They had a magnum of champagne and we drove around for quite some time while they did some illicit substances in the back. They tossed rolled-up $50s and $20s to me in the front seat as tip money. I dutifully brushed off each bill and added them to my wallet, pretending not to know what was going on.
But that’s not the most bizarre part. The “couple” argued on and off about showing up to the wedding because, apparently, she felt weird about getting married and he was trying to convince her it was a good idea. I finally dropped them off at the church and he slipped me a matchbook with his name and number written on it. Yeah, it was the late 80s and I was a young woman, one of the only female limo drivers at the time in that city.
I scored a sweet leather jacket with the tips from that night.
52. Cadillac Conversations
Many years ago, I had a security job that included the occasional responsibility of driving our rich clients around. I would typically drive them in my employer’s Cadillac Escalade that we had for those types of requests, so there was no divider between the front and back seat like in a limo. These were mega-rich people who treated me politely but quickly forgot I was present.
I overheard conversations about lots of shady and shady financial stuff. I overheard clients talking about insider trading, embezzlement, price-fixing, and stock pumping. I also heard some speaking openly about extra-marital affairs, intimate exploits, and expressing pretty disturbing attitudes. All of this was done with me sitting a couple of feet away in the driver’s seat like I was a piece of furniture instead of an actual human being with ears.
53. 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 from 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.
54. A Touchy Statement
I work in auto parts and a really flustered woman came in last winter. All she said was that she couldn’t see clearly anymore cause the things weren’t cleaning the glass. I go out to look at her wiper blades. It’s a newish Mercedes, and the rubber is torn clear off the frame. So, I go back inside and while I’m getting her replacements, I’m explaining to her how you need to free the blades from ice before you turn them on, or they’ll tear like that.
She gives me the most puzzled look I’ve ever seen on a person: think puppy hearing a weird noise for the first time, head cocked and all. She asks me what I mean… I said before you get in and turn them on, just give them a gentle pull so they’re not attached to the ice anymore. Her response made my blood run cold. She gives me that look again and says, “It’s cold, you can’t expect me to seriously touch it.”
Now it was my turn to be a little puzzled. She says, “I thought the car took care of that nonsense, you can’t expect a regular person to work on it like that.” I said ma’am, the only way to prevent this happening again is to ensure the blades aren’t stuck in ice…that’s it. She huffs out loud and says, Fine! I guess ill have to talk to the help about being on top of that from now on.
Then she pays and leaves before I can process and say anything else.
55. My Sister’s Keeper
My sister. She was loved and spoiled by my parents. They gave her any gift she wanted—shoes, a new phone, a car…even money when it was MY birthday. I, on the other hand, got the opposite. They told me I was selfish for asking for money. My mom rarely visited me or talked to me. When I had my tonsils and adenoids removed, there wasn’t a call, text, or visit from my mother.
Meanwhile, when my sister had hers removed, my mother drove her to and from the surgery. Heck, she even forgot my 14th birthday. When I saw her that Christmas, she laughed about it and said, “Oh, oops!” No money, no gifts. But when my sister’s 18th birthday rolled around, and she got $500. I never really ask for much. Not even the newest phones.
I’ve had the same $300 laptop for four years now; the same Android phone from that time, too. When I get money, I typically use it to buy clothes or the rare new pair of shoes. Sometimes, a new video game. Whenever my sister got money, on the other hand, she got everything she wanted. She once threw a fit when my grandmother didn’t buy her candy.
56. Poverty is Just an Aesthetic, Right?
My ex was a “poor” rich kid from the eastern suburbs of Sydney. His dad was the CEO of a big medical corporation, but my ex was a “free spirit, hippie” who would act like he was dealt a rough hand in life. He was smelly and dressed in what looked like rags—all for the aesthetic. His dad gave him $500 regularly to spend on whatever he pleased. He blew it all on drugs which he’d share with his hippie mates. He never had to work a day in his life and his parents paid for his university tuition upfront. But it got so much worse.
His mum ended up having a chat with me basically implying that her son couldn’t date me because I was poor. (I’m from western Sydney so if you know, you know).
57. Spoiled & Dumb
A kid in college was a roommate of a friend of mine. He was always bratty and spoiled but hung out with us as if he were a good friend and we let him chill with us because sometimes he wasn’t bad. Then one day we heard him arguing with his mom on the phone that he needed more money. From the ensuing argument, we learned that he had, in less than one year, burned through $30 grand that his parents gave him for food and discretionary spending.
Mind you, he was not paying for tuition, or lodging, or his car with this money. It was basically just food money, as all those other things were also already covered by his parents. He was calling his mother some really nasty things, and hung up on her. Then his father called and they got in an argument, cussing each other out.
At the end of that call, he threw his iPhone at the wall and shattered it (this was the original iPhone). Turns out they cut him off and basically he had to drop out of school and drive back home (out of state) because he couldn’t afford to do anything anymore (and of course was too good to work a pleb’s job).
58. Get Grown, Girls
While working in a casino here in Las Vegas, a herd of girls came to my window and one proceeded to tell me about her great birthday party itinerary that her dad had paid for. For her 18th birthday. With no adult in the party. Just a bunch of teenaged girls, out in Vegas, where none of them could do anything because none of them were 21.
I couldn’t even check them into their reservation without being 21. They start yelling and screaming at me, so I calmly call security—and security tells them they can either, “go play in the arcade,” or leave and try to find a hotel off the Strip that will take them in without being 21. The anger turns to tears. The security guard is unmoved.
59. Born to Spend
I had a classmate in college who was apparently some wealthy diva. Marries a guy whose parents were millionaires as well. Both eventually flunk out and tour the world on mommy and daddy’s account, soon getting married and have a child. They lived with his parents in a mansion at the time. It seemed like a dream, but it was actually a nightmare.
She gets tired of living with them and blackmails her mother-in-law to buy them a house or she will never see her grandchild again. His family refuses. Weeks of tantrums, Facebook and Twitter rants, eventually she moves out…to her own parents’ vacation home…oh, but it turns out she was actually just getting started.
A few years go by, and she is about to get cut off. So she has a brilliant solution: She gets pregnant again then goes back on social media to complain about how her family would abandon a pregnant woman and her child. Her parents crack and continue pouring money in. Husband’s family cracks and buys the home.
Now years down the line, I still see regular social media updates from her about overcoming adversity, triumphing over hardship, beating the odds, chasing your dream etc. etc. The married couple to this day has never worked or gotten a paycheck.
60. My Entourage Should Burn Carbs Too
I live in Hong Kong. Back in the early 2000s, a local gym/fitness club changed their regulations so that only people with paid up membership could enter the premises. Why? Because tai tais (a colloquial term in Hong Kong for a wealthy married woman who doesn’t work) were bringing their maids to the gym to help them undress and dress.
The (mainly) Filipino maids would sit in the changing rooms for an hour or more while their employer did a class, then help them dress (dry hair, etc.) when they came back. The gym basically wanted to get rid of the Filipinos sitting around in the change rooms, but the tai tais simply bought them memberships!
61. Daddy’s Dime
In college, I knew a girl whose daddy was some big shot banker or something. He made enough that the wife didn’t have to work and three kids could go to expensive schools. This girl didn’t have to work during college, had all her supplies and lodging paid for by daddy, and got to fly home every time there was a three-day weekend. All on her father’s dime.
I once had to borrow $10 from her to pay for some food when we went out to eat. I promised I would pay her back once I got my check next week—at the time, I worked for a cafe. She seemed cool with it. Turns out she was not cool with it, and promptly bashed me on her blog and to all her other friends calling me a bad person and a thief because I borrowed $10.
I paid her back. I brought up the blog posts and she was very embarrassed. The last I heard of her she’s living in a daddy-paid Manhattan apartment working part-time as a receptionist at a yoga studio. She started a new blog about “the struggle.”
62. The Garage is Open But Nobody’s Home
Rich kid in my high school crashed six cars within a year. And they weren’t like 1990’s Toyotas and Hondas most high schoolers buy (themselves); these were brand new Subaru STIs, a BRZ, a BMW, brand new Jeep, stuff like that. The last car his dad bought him was a semi new Ford focus. A decent car, better than my 1997 white Camry.
Every day he complained and threw a fit if his dad wouldn’t buy him another $30,000+ car. He always did.
63. Poor Little Rich Boy
I have a friend who is blissfully unaware of how utterly conceited and privileged he is. His parents buy him everything and he has never worked a day in his life. When we were in college, his parents got him this huge MacBook Pro with all of these upgrades. The screen was basically 4K. He boasted about how much all of this cost.
One day, we took a day trip to this really nice mall, and we visited the Apple Store. We walked in and it was pretty packed. He looks at me and loudly says, “It feels so good walking in here and knowing I have the best and fastest laptop.” Not even a month later, he broke the computer. Recently, he graduated college and his parents got him a brand new 2019 Dodge Charger. We went to a friend’s grad party, and he somehow made the conversations about the car and asked everyone if they wanted a ride.
At the same party, the other friends’ parents surprised her with travel tickets to visit Europe. Her dream trip. Knowing her family, only I knew the heartbreaking truth: they must have scraped the funds together for this trip. My friend was so happy; she and her family were hugging and having a really good moment together. The conceited friend ran up to the family and started saying stuff like, “Oh you’re going to Europe? It’s so great! When I went I saw etc. etc. etc.” basically turning the moment revolve around him.
64. I Fought For This!?
My dad owns a bar, and one night there was this rich kid with his friends. Boat shoes without socks, the whole thing. He was giving one of the bartenders a tough time because he was on the shorter side. This kid was bothering the bartender for about half an hour until finally, he got my dad to come out and deal with it.
My dad basically yelled at the kid about how the bartender enlisted in the military and fought in Afghanistan and how ashamed he should be to make fun of an honest, hardworking veteran for his height. The kid left the bar nearly crying, and I hope that experience helped him change for the better. Don’t mess with veterans, kid.
65. You Can Take Home with You
I should preface this saying I was born to a very wealthy family, though one who put a great emphasis on a strong work ethic and that eschews attention or special treatment. That being said, having grown up around people of great wealth my whole life, I can honestly say their entire reality is different from most peoples. They are accustomed to a certain lifestyle that most people can’t fathom.
Take my best friend, for example, he has been in South Carolina all summer at his 15,000 square foot “beach cottage”. When he shows up to his house in June, he wants no transition period. That means no spending the first few days getting the summer house ready, unpacking, going to the grocery. He wants his life no different when he boards his Citation X in TX than when he lands in SC.
To achieve this, he has a handful of employees go a week ahead to SC and get everything ready. Deep clean the house, polish silver, manicure the grounds and on and on. They go to the store and buy food, drinks and all the sundries one would need for a summer vacation (sunscreen, toothpaste, etc.). They start unpacking the packages from Neiman Marcus containing his wife and kids’ new summer wardrobes that they have never even seen because they were purchased by their private shopper/stylist.
They train any new summer help and those who are staying with them, like the chef and a personal assistant, or two, move into their small house a few miles away. Cars are readied, boats are docked activities are planned all so that he and his family do not have to waste time enjoying their vacation. For a summer spent at this lavish estate and having a rotating cast of family and friends come and visit, I imagine it costs about one million dollars, not including private jet airtime or normal house maintenance.
I was just there last month and asked to use a car to go play some golf, five minutes later there was a Chevy Suburban parked out front with our clubs already loaded. I go to put the car in drive and notice it only has 87 miles on it. It had just been purchased the day before in anticipation of a large group coming to visit. His time is valuable, and he chooses to spend it a certain way.
His “disconnect” from reality can be seen in how there is this massive effort behind the scenes so that he is not inconvenienced with things that most people would find mundane. Yes, it costs him millions of dollars to never have to go to the grocery or fill up with gas, but he will tell you it is worth every penny.
66. Nice Try
I was a host at a local mom-and-pop breakfast place in San Francisco for 7 years. Despite being small it catered to a lot of high-end people like the Mayor and professional football players. So we’d end up with an hour or more wait sometimes on busy brunch days. My favorite thing that people would do is pull the “I know the owner” card to try and get a table. But there was just one problem.
They were totally unaware that the owners both worked the line everyday and were right next to us. So I would respond by saying: “Oh, let me get them. I’m sure they’d love to say hello!” The looks on their faces when the owner would come out and say: “I’m sorry where have we met?” was priceless. It was one of the only restaurants I’ve ever worked at that cared more about their staff than the customer always being right.
67. A Little Harsh
I worked as a waitress at a fancy bed-and-breakfast when I was 20. We hosted a date-night special and it was completely packed with couples. There was an older married couple that was in my section and the husband was super nice. He asked how my night was and even postponed his order so that I could clear a nearby table.
His wife had a permanently angry face and glared at everything I did. After their meals were cleared, it was time for dessert and champagne, as per the date night feature. She orders a brand that technically isn’t champagne, it’s a sparkling white wine. I didn’t want them to feel ripped off so I told her: “That’s a great choice but just so you are aware, this is sparkling and not champagne. Is that okay?’
She looked at me for an uncomfortable amount of time. Her husband is looking at her with an expression of mild concern. Well, her brain must have been going into overdrive trying to think of something insulting, because after a long silence she says the meanest thing: “Sweetheart, I see how hard you’re working. Have you considered getting some work done? You wouldn’t have to work so hard if you were a little prettier. Just a thought…”
I could not even process what she said until I got to the kitchen. Her husband’s face was what made me cry. I can take an insult but the mix of embarrassment and shame on his face just made me lose it. I comped his dessert and made her drink with mostly apple juice. I hope that $27 glass of 80% cheap apple juice was good.
68. Your Loss
My wife and I had a gift card for this high-class restaurant that we got as a gift from a well-off friend. So we go to the restaurant and have a lovely meal. But when our meal was over, things went sour. My wife wondered out loud if we’re supposed to pay at the front or at the table. The waitress comes by and overhears us talking about our gift card and she says, “You can give your COUPON to the gentleman over here.”
Then she ROLLS HER EYES. My wife and I felt really embarrassed and we sheepishly left our table. We went to the gentleman at the front, and he was very polite and gracious. I can tell from his behavior that she does this a lot. We left a standard tip to the waitress, but we left the gentleman 25 bucks and the chef 50. Too bad for her!
69. Childish Dad
I was working a catering job for a 4th of July party at an exclusive yacht club. I went about my business and was clearing used plates from tables. After stacking as many plates as humanly possible, I turn and start walking back to the kitchen. Next thing I know I feel something hit me in the back of the head. It was a chicken bone.
A grown man had been watching me the entire time, with his four-year-old son at his side. Apparently, he decided he didn’t want to wait the five minutes it would take for someone else to come by and clear his table, so he chucked his garbage at my head. And then he pointed at me and cracked up. I calmly set down my tray and just walked out of the restaurant without saying a word.
70. Café Society Girl
There was only one coffee shop on my campus, which operated out of the library building. It was always crowded. You pretty quickly learned that if you wanted coffee before class, you got there 20 minutes early, grabbed a newspaper, and took your time. It was always funny watching incoming freshmen crowd the line five minutes before their 8 am class and slowly filter out in despair.
Cue this little freshman girl walking up, assessing the line stretching out the door, and boldly deciding to just sorta…skip it. Now, the baristas were usually pretty cool with people skipping for simple things: Dropping a buck for a cookie, anything that didn’t require interaction. Not this girl. She caught the barista’s attention, while the previous customer was still paying, and went:”Hi, yea, can I get a latte please, like really quickly?”
“Umm, the line starts back there,” replied the now slightly confused girl behind the counter. “But I have claaaaass” whined the freshman. There was an awkward pause before the barista responded with a brutal retort, “You are on a college. campus. Are you freaking serious?! Why do you think all these people are here?! Back of the line!”
“Oh” was the only thing the freshman girl thought to say. As she turned to look at a line full of people staring daggers back at her, she looked not upset or embarrassed, but sort of enraptured by this newfound understanding she’s just been imparted. It’s like for first time in her entire life, she realized that other people were in her way for reasons.
It was actually kind of beautiful to watch, like a baby deer learning to walk for the first time. Better late than never.
71. Did I Do That?
Somewhat distant relative spent all of his university years and twenties partying hard with the ~$100-120K allowance his rich company-owning father gave him each year. He’d travel the world each year going to Bali, Thailand, Europe, every year Oktoberfest, just rampaging. At 32 or so he decided to settle in an upscale ski resort area of the US and open a business with his hot gold digger fiancé.
When he went to transfer his money to his US bank account, he noticed it only came to a few thousand dollars. He angrily asked the bank worker why she hadn’t transferred the entire amount only to be told that that was the entire amount. His father had cut him off without saying anything and he just hadn’t noticed. Absolute flatline.
72. Geography Lesson
I worked at this fancy event center where a bunch of yuppies host their weddings. My job was so easy; I literally just opened doors or clicked buttons on the elevator. One time, a man who I had previously opened the door for had come back to talk to me. He proceeded to ask me where I am from and what I thought about him adopting a daughter from Korea.
I am an Asian American, born and raised in the United States, so I responded with something along the lines of: “Yeah that’s really cool..good for you.” He kept asking me uncomfortable personal questions about living in Korea and made offensive comments. For example, he said the fact that I could fluently speak English was amazing.
The funniest thing is that I’m not even Korean, I’m Cambodian! I told him this, and that Korea and Cambodia are very different places even though they are both in Asia. I come from a very educated and upper middle-class family and in times like these, I literally feel like they think I came straight from the slums or something.
73. Excuse Me!
Once I had a job as a cocktail waitress at a bar in Hollywood. It was very “A-List.” We served movie stars and celebrities there all the time. It was a very busy Thursday night and I was running drinks back and forth from the bar to the tables. One of my tables had about five glammed up women that looked like they were on a girls’ night out.
They were probably in their late 20s and they obviously had money, I could tell by the purses, shoes, and snotty attitudes. I put their order in for their second round of drinks and I’m rushing by their table holding a tray full of drinks including martinis going to another table. The one girl decides she wants to change her drink order so as I pass by her, she turns and grabs the back of my dress to stop me so she can change her order.
Of course my tray tips over when I’m jerked back and the drinks crash all over me and onto the floor. I turn and give her a withering look but she barely makes eye contact and says: “Instead of a cosmo I want a vodka on ice” and turns back to her friends as if nothing happened. I was very tempted to spill some drinks on them next!
74. Wrong Side of the Bed
A kid that used to work for me came in to work super cheesed off one day. I asked him what was wrong. I’ll never forget his words. He replied, “My freaking maid didn’t make my bed again, but my dad still won’t fire her!”
75. Baby Steps
My best moment was when I got hired by a pair of Woodside, CA parents to transition their horrible 18-year-old into the realities of “real life,” something that evaded both of them. My first action was to take away his platinum, limitless credit cards. He threw a tantrum that lasted several days. “Where am I going to get money?”
Get a job. “My parents will fire you.” They didn’t fire me. When he realized that boundaries and budgets had been set in stone, and that he not only had to pay the bills the rent but taxes too, he headed straight to college to wait out the next four years. He is still a little jerk, but at least he has a job and an education now.
76. 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.
77. It Should Be Illegal to Be This Rich
I used to intern at a law firm that dealt in tax and estate management for “high net worth individuals.” Given the worm’s eye view of the place that I had, I could only ever catch glimpses of our clients’ crazy; but suffice it to say, their stories are absolutely insane.We had a respected spinal surgeon who became convinced that he no longer needed to sleep or eat to survive. Oh, it gets worse.
Instead of sleeping, he would meditate for two hours a day and would eat vitamin pills instead of food—except for when he came to town for a meeting and made the firm take him out for a steak dinner. He was performing two or three operations a day in this state. We also had a powerful CEO, who became convinced that her rivals were trying to cast black magic curses on her and her family.
She paid our $600-an-hour attorneys to investigate shamanism for her to get to the bottom of it. We had another client, who owns a major restaurant chain and who shot his neighbor’s dogs for coming onto his property. The neighbor was also wealthy, and they both owned several hundred acres of land with no fence between them—and there was no livestock on the property, so he wasn’t exactly trying to protect his chickens either.
Not a client per se, but the wife of one of our clients ordered a hit on her husband. The hitmen she hired were so laughably incompetent that they didn’t even come close to killing him. On the first attempt, they shot out the windows of their house on a weekday afternoon when he was at work; the second attempt, they tailed him for a few miles but never did anything.
She got so frustrated with their incompetence that she fired them and hired another hitman, who turned out to be an FBI informant. The reason for the hit? They had just started divorce proceedings, and he was already seeing another woman who she feared was going to get her divorce settlement, which isn’t even a thing.
I wish I had more but as an intern there I had very little client interaction and got most of this through hearsay and digging through client files for our attorneys.
78. Prove It!
I work at a pretty high-class seafood restaurant in Rhode Island and one evening I had a table of people who had all ordered a lobster dish. I went to clear their table and one of the men complained that the lobster was not fresh and was frozen. I politely informed him that the lobster was never frozen, but he was very adamant.
So I said I was sorry and walked off, and I passed my manager and mentioned it to him. He stormed off and came back five minutes later with a cardboard box full of live lobsters and said: “Go show them!” I walked back out to the table and set down a box full of 10 or so lobsters and said “See. Fresh.” The guy’s dumbstruck face was so satisfying. The tip…not so satisfying.
79. Act Your Age
I umpire little league baseball and was calling a game between a couple of pretty snooty leagues. After I called strike three on a kid, the mom yells from the stands: “Don’t worry honey, he’s just some fat loser with nothing better to do!” I looked back to see who said it and saw that she was a young, rich looking mom, probably about 35 years old.
I knew then that I’d make her regret her words. This woman clearly prided herself on how she looked, considering she was pretty dolled up for her kid’s little league baseball game. So between innings, I leaned back against the fence and said to her “Ma’am these are children. I’d expect a woman in her 50s to have a little more class than that.”
80. You Can’t Buy This Kind of Friendship
“Why would you take the train?” This a sentence that led me to believe that a lot of rich people have lost touch with reality. Though they can still be good people, as I learned over the week. Several years ago, I was a contractor in Afghanistan. I was in my early 20s and making a bunch of money. I decided I’d go to the Monaco Grand Prix. I flew from Dubai to Paris then to Nice.
On my flight to Nice, I sat next to a Jordanian guy in his mid-30s. I could tell he had money because of his Patek Phillipe watch that probably cost around $50k. We got to talking, and I jokingly said, “Nice watch. Private jet in the shop?” He laughed and said, “Actually my father is using it, so I have to fly commercial.” We chat for the rest of our flight about attending the Grand Prix and movies and whatnot.
When we go to get our bags and I say my goodbyes. I tell him I gotta catch the train to Monaco that’s leaving soon so I can get to the cheap apartment I rented on the edge of town. He looks at me and just says “Why would you take the train?” I tell him I can’t afford a taxi, so I have to take the train in. What he said next blew my mind. He just says to take the helicopter with him.
I put up a half protest (who wouldn’t want to take a helicopter into the city?!) and eventually go with him. It ruled. He had his driver, who drove a freaking Rolls Royce, drop me off at the apartment. We exchanged numbers, even though I never expected to hear from him. The next day he invites me to the docks to attend a private party on a yacht. Lewis Hamilton was there!
What was originally supposed to be a few days of me hanging out and watching the races from the stands turned to me attending parties with celebrities and Formula 1 drivers and the richest of the rich. Hanging out in the pits and all sorts of cool stuff. On one drunken night, he confessed his secret. He said that he invited me because it’s the first time in years someone treated him like a person.
Not kissing his butt or being fake. I sort of felt bad for him. He didn’t seem like he had any real friends. I’d be lying if I wasn’t envious. But little things he said made it seem like he was completely oblivious to how everyone else lived. But I don’t think I can really blame him.
81. You Get What You Give
A very wealthy couple I was friends with some years ago offered to take me to a legendary, top star Italian restaurant in the city with my best friend and her husband. They offered to foot the whole bill since there’s no way that I or my friends could afford that kind of place. I didn’t think my best friend would be so affected by the experience.
She told the waiter she didn’t understand why she needed a menu when they should just “intuitively design her food experience for her.” I thought I would die of embarrassment. I had to hand it to the waiter though, he said “Very well ma’am”, took the menu and came back with a plate of spaghetti and meatballs for her. We all laughed out loud.
82. Hitting The Bar
Through past work, I met a guy who asked if I would be interested in some extra bar work at his house occasionally. I said that I absolutely was, happy for the extra cash and change of scenery. So, for the next about four years, I would turn up at about eight, along with a few tools of the trade that I favored, and head through the beautifully disguised secret door.
This led down to what amounted to a self-contained underground house with a fully stocked bar, ice machine, etc., where I would make cocktails for the participants of these periodic “special parties.” From about nine, couples, some in little masquerade masks and little else, would arrive and mingle and then vanish and reappear, with a different thirst to quench.
I worked for barely five hours; it was hardly even work. It was an insight into a world I would never know. Afterwards, he came over, fully dressed, thanked me and gave me an envelope with cash. He also mentioned that I may have recognized a few people and that they would appreciate it if that fact remained undisclosed.
I assured him that I hadn’t saw a thing, like I was in some terrible movie. My five hours of work made me more than I make in a week. Next day, I got a call, asking if I could come over, just for a few minutes. I was off, so I headed over. He greeted me at the door, brought me into the hall, and said that the guests wanted me to have that, and hoped they would be seeing me again.
It was another envelope with the same amount as before. Every few months for the next four years this was repeated. Until I couldn’t do it anymore. I can’t describe why, but I would dread the call. I think being part of something that was so throwaway to them while I was living off a bag of change was, at times, just depressing.
83. Foul Flowergirl
I went to a wedding a few years ago, and one of the bride’s younger female cousins was beyond obnoxious. Her mother was even worse, which is why I imagine the little girl was this way. Over the course of the afternoon, I heard her say such gems as, “I would NEVER shop at Walmart. All MY clothes are name brand.” She was a complete nightmare.
This was said to a seven-year-old girl in a very cute dress, which she proudly proclaimed her mother bought her at Walmart on sale. Later, while eating cake, the little brat said something way worse. She took some of the 7-year-old’s dessert, stating that “It’s for your own good, you’re too chubby.” The one that really got to me, though, was when she started boasting that she was going to catch the bouquet.
Every adult in the place was severely annoyed by her at this point, and I made it my mission to catch that god darned bouquet. When it came time for the tossing, I centered myself and gave a wink to my friend, the bride. She threw it right at me, and the little 12-year-old lunged for it. I elbowed that brat right in the face, and caught the flowers. Not even a little remorse.
84. I Prefer to See the Wallet as Half Full
Somebody told me about a guy bragging about spending $100 on a bottle of wine. I thought we were on the same page (what an idiot, right?) but I was so, so wrong. After I started making fun of him for paying too much, she told me “Everyone knows good wine is $100 a glass, not a bottle.”
85. VIP Guest
I was working as a server, and one night I brought water and menus to a table and asked if the guests would like to order drinks right away. The man glared at me and told me that I’d have to do better than that if I expected a tip. He wanted the best service. I was a little befuddled, smiled, and said that I’d do my best to make his visit an enjoyable one.
He said loudly: “Do you know who I am?!” When I admitted that I did not he was really offended. He then informed me that he was a professor at the community college the next town over. Seriously. The community college. His wife was shushing him, turning beet red, and face-palming the entire time. That poor, poor woman.
86. The Toughest Customers Cost the Most
There is this lady that comes into my store who is so awful, just seeing her makes my blood boil. As far as I know, she has let her kids destroy the store. Literally throwing merchandise all over the place. She’s asked for someone to get a key for the perfume case—then whenever someone got there, she decided that she wanted to shop more.
She brings an entire cart full of stuff to check out and then halfway through the transaction, she goes to get more stuff, sometimes more than once in a transaction. She REFUSES to read stuff on the packages. I seriously had to read the differences of two items to her. She once had me figure out what kind of batteries an item needed, get them for her, and then put them into said item.
She frequently had us check the back for an item we told her we no longer carry. She insisted that we check regardless. She left her child throwing a tantrum right in front of the register so that no one behind her could check out. And, as if that weren’t enough, she asked me to go get items for her while I was checking her out.
Keep in mind that this lady isn’t old, maybe mid to late 30s. My manager said that we would honestly tell her to never come back if it weren’t for the fact that she spends so much money at our store.
87. Snobette Snootyson
I was on my high school’s newspaper staff and we always did a section on cars in the parking lot, where we highlighted one old beater and one super nice car and then interviewed both owners. Everyone loved it—and don’t worry, the owners of the beaters were always super excited to be a part of it and they always had the best stories.
So we pick Snobette Snootyson because she’s got a nice brand new Range Rover or something, and after I’m the last to call “not it” I’m forced to interview her. I asked her what was her favorite feature of the car? “Well one time I forgot to put it in park and it started rolling away, but it didn’t roll that fast so probably that. Or my G-Eazy bumper sticker.”
Then I asked, “Got any funny stories about your car?” “Yeah!” she exclaimed. “When my parents first got me it, I was making faces at my friend and turned left when it wasn’t a green arrow and totaled it. So they got me the same one again!” I managed to sneak into the article: “Snootyson has managed to keep her car undamaged since October.” It was January.
My sister has no job and lives by herself in my parents’ summer condo. She drives my parents old car, doesn’t pay any bills, and squanders all the money my parents give her for food and “emergencies” on partying and going to bars. She refuses to apply for anything that isn’t a “glamorous” receptionist position for at least 17$ an hour because she’s too good for it, despite having a worthless degree from a joke private school.
She has a new garbage boyfriend every other week. She is also incredibly mean. She never has anything nice to say to my parents or other siblings and constantly criticizes them to their faces and behind their backs. The last thing we trusted her with was picking us up at the airport (literally 30 minutes away from the house), for which we gave her a week’s notice and texted her every other day to remind her.
We land and she doesn’t answer my calls; then she calls my mom to complain and my mother starts yelling at us for “ruining my sister’s night.” My sister then sends us a bunch of text messages saying how disrespectful it was for us to ruin her weekend by expecting her to stay home to pick us up instead of going out. It was like 7 pm.
She could have easily gone out after. We had to take the train and it took us three hours to get home. I am never speaking to her again.
89. 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 them.
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.
90. One Man’s River is Another Person’s Bathtub
I repair bathtubs and showers. I’ve been in poor homes, middle-class homes, wealthy homes, and super mansions. So, we were at this mansion, the kind where there’s a tennis court and pool in the back yard. The kind where the foyer and first room of the house had 16×16 black granite tile with subfloor heating. Just this magnificent house with its three-car garage; but in the garage, there were three lifts to literally stack their vehicles. These guys were loaded.
They are “updating” the house to sell so they can move back to North Jersey. They replaced the soaking unit in the master. The granite in that bathroom was absolutely breathtaking. It was blue, and under a certain light sparkled like there were lights built into it. The deck was cracked at the caulk line. So, we’re in there fixing it, being as anal and meticulous as possible because we know we’re in probably the most expensive house ever.
The wife comes in to chat with us and basically states that they just got the same kind of soaker as before because it’s the only thing that fit in the spot. Eventually, she says something like, “It’s okay though, it was only $8,000.” If I was drinking something, I’d have choked on it. She said it like the tub was a piece of trash that she settled for because it was cheap. $8,000 was a drop in the bucket.
91. A True Man Child
I had an old friend call me in the middle of the night, begging for me to go pick him up. I thought he had gotten mugged or something along those lines. The actual reason was jaw-droppingly ridiculous. Turns out, he got into an argument with his parents because they bought him a storage space for him to put his childhood items into.
He was so upset that his parents decided to sell their home and move elsewhere to retire and that he would be forced to decide which of his items to keep and sell. I deleted his number right after that night and have avoided him at all costs since then. He is 29 years old and a total man-baby. Like seriously dude, work on your drama.
92. “Stunning Privilege”
I’ll throw out the disclaimer that the guy wasn’t a jerk, he was okay, but the stunning privilege was both jaw-dropping and hilarious. He was a guy in college who came from a pretty wealthy family. He never had a job before—which isn’t that crazy for his age and being a student, though I had been working throughout college.
One day he decided to get a job because he was “bored and wanted to see what it was like.” I forget where he got a job, but it was a pretty laid-back part-time job pushing paper in an office setting. A few weeks after starting, we’re hanging out, and he’s talking about work. He reaches in his pocket and says, “Today they gave me this. What am I supposed to do with it?” It was his paycheck.
I stared at him for a second and said, “Dude, that’s your check. What do you mean ‘What do I do with it?’ Deposit it in your bank.” He says, “I don’t know how to do that. My dad just puts money in there. I don’t look at it, I just take money out from ATMs or use my card.” Not wanting to walk the poor guy through such an easy process, I just tell him to take it to a grocery store and cash it.
What he said next made me nearly fall off the couch in disbelief. He said, “What do you mean cash it? Like, they’ll just give me money for this [looking at his paycheck]?” Must be nice.
93. Too Little, Too Late
I was working as a General Manager at a struggling restaurant—struggling despite excellent business, because the owners would do stupid things like take trips to Italy on the company dime to source the “perfect” panini press. They also wouldn’t staff properly; I was the only waiter ever there, open to close, six days a week, on top of handling phone orders, inventory, and other managerial duties. I was wildly overworked, but I sucked it up because the base pay was good, plus tips.
However, to fund their lavish “business” trips, costs had to be cut at the store. They decided to do this by bumping me down to minimum wage for tipped employees—effectively cutting my salary to 1/10 of its previous level. They were also too chicken to tell me until I got my new teeny paycheck and questioned the mistake. “Oh yeah haha, forgot to mention that blah blah cost-cutting blah valued team member please work with us through this difficult time.”
I had worked for two weeks at this new lower rate without my knowledge. Pretty sure that’s illegal, but hey, a lot of illegal things go on in the restaurant industry. That’s not when I rage quit, though….a couple of hours later, I’m fuming and have decided that I can’t work for the lower rate, so now I’m just waiting for the perfect chance to give my notice.
They called in a delivery guy who was fired a few weeks before, and they talk about hiring him to start doing our Facebook posts and handing out flyers around town. Whatever. Then I hear them offer him close to my old salary as “Promotions Manager”! What??? I was basically running the place for $2.13/hr and you’re offering this dude almost $20/hr to walk up and down the street saying “Eat at (Name)”?
And yet, it gets worse.
They bring up our negative Yelp reviews and this guy suggests asking friends to post positive ones. The boss starts laughing and says “Better not ask our waitress to post one, it’ll be all boohoo don’t eat there, I can’t pay my rent this month because they cut my pay without telling wahhhh!” I don’t think I was supposed to hear that, but I was five feet away, so of course I did.
I RAGED! I quit on the spot, told them to screw their job, and wished them good luck keeping the place open without me. They quickly realized I was right, as neither of them knew how to do more than pick up the takings once a week. They begged me not to quit. They were so desperate that they sat there for half an hour and allowed me to bluntly tell them exactly what kind of huge idiots I thought they were in excruciating detail.
I went on and on as my rage burned, and they just quietly listened, nodding and apologizing. Once I had cursed myself back into calmness, I walked out, 30 minutes before the dinner rush began, leaving them with an unstaffed floor and no clue how to even open the cash register. God, they were morons. I loved that they actually listened to me telling them exactly how stupid they were. No repercussions on my side, as the restaurant industry isn’t known for checking references.
The place closed down about 18 months later, and I was surprised it even made it that long.
94. A Meal To Remember
A cousin works at a branch of a higher-end, world-renowned hotel chain, in a large US city. A couple of years ago, a guy came up to him and asked him for a dinner suggestion and said the price wasn’t a concern. My cousin keeps up with what’s trendy in the city, knows some owners and such, and gave the guy a suggestion.
The next day the guy asked for him by name, gave him $100, and said that the dinner was amazing. He went on to ask where they should eat that night. Another suggestion and the next day, another $100. Only this time, his manager saw this go down and, a few minutes later, asked my cousin, “Do you know who that is?” He didn’t.
It turned out that he was a well-known old money guy. But that was just the beginning. A couple of months later, my cousin went to work one day and was told that this person would be calling at 6 pm, and only wanted to speak to my cousin. The conversation was short, basically along the lines of “we’re in town next month for four nights, book the six of us four wonderful dinners, we trust your opinion.”
He was given an email for their family assistant, and to let that person know the plans. The family arrived, said “hi” to him as they checked in, and said they were looking forward to their dinners. Four days later, while checking out, they handed him $1000 “for his wonderful local knowledge.”
95. Throwing The Baby Out With The Bathwater
I’m a retired paramedic. I’ve seen a lot of messed up stuff—but one moment was worse than all the rest. I was once told to immediately place a freshly delivered newborn baby back inside of its mother’s body. She delivered in a transport ambulance en route to the Weill Cornell Medical Center. She then lost her mind over the fact that her baby wasn’t born in a hospital and, furthermore, not born in a good hospital.
As a result, the mother then told me to “hold the baby in with your freaking hand!” I explained that this wouldn’t work and that we were having this child on 3rd Avenue. She completely flipped out and started yelling at me like a complete lunatic. Finally, she and I made an agreement that I would say that the baby was still inside her body until we backed up at the hospital driveway.
I guess this satisfied her requirement of her kid being born at a hospital versus next to a dry cleaner’s on 3rd Avenue. So, as far as that kid knows, she was born in the Weill Cornell Emergency Room Ambulance Bay. She will never have any idea how much turmoil surrounded her birth, and how unreasonable a request I was given in the process.
96. 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.
97. Missing Fairy Godparent
A colleague of mine used to be a bouncer at a club that was the place for rich kids to hang out. He saw a lot of the typical “look at me I’m so rich!” behavior. Things like buying the most expensive champagne in the club and telling the bartender to pour it down the drain, wearing several Rolex watches and handing them out like candy to strangers or tipping the staff thousands of dollars were not uncommon.
The thing that stuck with him the most was just how far removed these kids were from reality. In particular, one disturbing incident stood out to him. One night he had door duty and didn’t let a kid under the influence into the club. So, what did the kid do? He decided that it was a good idea to take a swing at him. It turns out that it wasn’t a good idea.
The kid found this out quickly after he was lying face down on the ground, handcuffed with his hands behind his back. But even now the kid didn’t seem to be too worried, he just kept saying, “It’s all right, just call my dad and he’ll sort this out,” over and over again. He seemed incapable of realizing that he was actually getting arrested for attempted assault.
Not even when the authorities finally arrived and put him in the back of their car did he seem to fully grasp the fact that he was actually in trouble and that his dad wouldn’t show up, wave a wand, and make this all go away.
98. Hotel Havoc
I used to work as a front desk agent at a boutique hotel. A guy who was obviously very full of himself came in with an online reservation that he had booked at a shockingly cheap nightly rate. He proceeded to give me a hard time about EVERYTHING, from telling me he shouldn’t have to give me his credit card info since he had prepaid his reservation, to telling me “Um yeah, I’m pretty sure I can find the elevators, I’m not stupid.”
He was just being an all-around jerk. About 10 minutes after checking him in, he came down and demanded that we give him a bigger room with a king bed and a view, even though he had booked a standard queen bed online. I complied, as we had extra king beds available. 10 minutes later, he came down again to complain about the size of the room.
He told me, “I’m only going to give you one more chance to make me happy,” and asked for the general manager. After much arguing between him and my manager, we ended up giving him our nicest suite AND free parking since we had “Given him trouble.” He got all this for a way cheaper rate, like $40 per night! Oh, but he outdid himself.
Get this: He informed us shortly after the ordeal, while on his way out to dinner, that he was not even going to be in the room for the majority of his stay, as he was visiting friends and would be staying at their home. What the heck! So I made it my personal mission to make his life a living nightmare from that point on.
I reset his room keys every time I saw him leave the hotel—which was quite frequently, 3-4 times a day. It was particularly funny when he came back tired from a night out and had to come all the way down to the front desk to get his keys fixed. Needless to say, he was very frustrated by the end of his stay. I doubt he’ll be staying with us again.
99. Side Chicks
When I was a poor college student my wealthy cousin and his wife went on vacation and offered to let me house sit to give me a break from my three slovenly roommates. They live a few towns over in a very nice house with a huge front lawn and a fancy, tall iron fence with double gates. The fence and gates are about 11 feet high. You have to have a remote to open the gates.
That first night I slept so well! I breakfasted like a king and then drove to school. I got back around five, made a supper fit for a king, and settled down to write an Econ paper. My cousin has a warning system for when someone driving turns off the road and comes up to the gate. There’s a chiming sound and you can look at screens in a couple of different rooms to see who it is so that you can buzz them in.
I was deep into my paper when I heard the chime. I was confused at first and check my phone before I realized what it was. I looked from the sofa and could see a movement on the security screen. I stood up and got closer and had a clear view of two women getting out of a white car. One tried to squeeze between two bars of the gate—impossible—and then the other woman tried to boost her over the top of the gate—hilarious.
The top one fell and even from the house I could hear swearing. I was about to press the intercom button and ask WTF was their problem but I was chuckling at their antics and just watched silently. They peered at the house intently from between the bars like a couple of jailbirds for a while. The skinnier one actually stripped down to her bra and panties and tried to squeeze through the bars again. No dice. Butt and boobs were not allowing that to happen. More swearing.
Then, as the skinny one got dressed again, the bigger one went back to her trunk and got out a tire iron. As soon as she started with the hinges of the gate I was calling 911. The cops took too long and the women left. I showed the cops the video but they couldn’t get a license plate number. When my cousin and his wife returned the next week I told them what happened and we watched the tape. He said that he had no idea who the women were but his wife looked pissed. I packed up, thanked them for my “vacation” and left.
She divorced him that summer.
100. Helicopter Parents Never Fly Coach
I worked as a nanny for a 1% family. The stuff I saw haunts me. I remember having one parent complain how rude it was a friend hadn’t offered to fly them to Miami on a private jet for a weekend getaway, and they were “forced” to go first-class. Had the other parent tell me they thought it was really “sweet” I was happy to help others and never be wealthy.
They would also spring last-minute trips on me and their kid all the time, so I’d stay in the main house with their child while the parents were country-hopping. Poor kid never had any sense of who was going to be where. There were business-related videos of the parents on YouTube, so it got to the point where I’d play them on an iPad so the kid had some sense of consistency.
Just to be clear, the kid was absolutely adorable and very sweet (which made it really hard to leave, I felt terrible), but it was pretty disheartening to think they’d probably turn out like their parents in a few years. The best part about the parent complaining over the first-class flight was when they asked me if I thought they were overreacting.
Literally asked me “Wouldn’t you be upset? Don’t you think that’s rude? They’ve been doing better [financially] now that they have Company X money they could have sent a plane etc.” and I’m thinking, well I’m pretty sure my entire year’s salary couldn’t pay for one chartered flight, so you know I’m probably not the best person to ask.