More money, more problems—or rather, more cluelessness. Money doesn’t always tank a personality, but some rich people run the gamut from oblivious to full-on mean, with too much cash causing an extreme case of “foot in mouth” syndrome. While most of us don’t run into spoiled brats too often, these everyday people witnessed the one percent’s most outrageous moments and shared their thoughts on Reddit. I hope you’re hungry because after these stories, you’ll want to eat the rich.
1. You Can’t Bargain With the Skies
Upgraded to first class recently on a flight that ended up delayed on the ground for an hour. I wasn’t even mad. A woman in front of me turned to her husband at one point and said, “Why don’t you go have a word with the captain and see if you can get him to hurry up? Tell him who you are.” There was just one problem.
I had no clue who he was and I don’t think anyone else would have either. But at least the guy understood that that wouldn’t work even if the woman he was with didn’t. He refused.
2. I Got a Golden Ticket
My classmate got three traffic tickets in two consecutive days. About $700 total, including fees and whatever. His response was disturbing. He just paid the fines without batting an eye and then cheerfully said it was a good lesson to learn. Pretty sure I was more appalled and upset about the whole thing than he was.
3. Two Hundred Reasons Why
I once asked one of the directors of my company to spot me for lunch because I had forgotten my wallet. He handed me two $100 bills and was legitimately concerned that it might not be enough.
5. Fast and Furiously Spoiled
In high school, this one rich kid was bragging that he got in his third fender bender in his “old” car (three years old) that his parents gave him, but he hated, so his parents were buying him an entirely new (current year) car to incentivize him to drive better.
4. The Cost of Opportunity Is Steep
My uncle who is really rich gave me some really great career advice. He told me that if I wanted to change fields, I should “just” take an unpaid internship or beg to work for free. Well, I need to pay the rent, so I don’t really have that option.
5. On a High (Income) Note
I have some very wealthy extended family. One of them recently purchased an $80,000 violin for their teenage son. I remarked that it seemed pretty excessive, especially because he had exactly zero plans on playing it after he was through with high school. Her response made my blood run cold. All she said was, “Well, what else was I going to spend it on?”
6. Save the War for Home
Went to a destination wedding in a Mexico resort. Rich kids rented a golf cart, tore through the streets and flipped the cart (injuring people and causing a huge commotion and traffic jam). A Mexican lady comes out and begins to scold them for their behavior. “You wouldn’t act this way at home!” I could not believe his answer.
He just looked at her and said, “I promise you we do.” It was the earnestness of his reply that got me. He really believed that he was placating her with that response. There’s gotta be a German word for something being funny because the other party is aloof to their own behavior.
7. She Nailed It
I work at a veterinary hospital in a fairly wealthy area. Once had a client hand me a $50 for a $9 nail trim on her dog. I told her the price and she just shrugged, told me to keep the change and said that would be my lunch money for the week. Sad thing is, it was.
8. Let Him Eat Bread
I was flying a private jet, and the caterers forgot the owner’s sandwich. He graciously said, “No big deal” and I replied that I’d call when we landed because they charged us $100 for it. He said “Is that a lot? How much does a sandwich normally cost?”
9. Taking the High-Cost Road
I used to work as an after-school babysitter for a LOADED doctor couple with two kids. My job was mainly to pick up the younger kid from school and hang out till his parents got home. He was a good kid, but coddled and immature. He was in fifth or sixth grade at this point. Oftentimes he would not be at his classroom when I came to get him, and the school campus was huge. I’d have to run around searching for him. But that’s just the beginning.
A few times, I got ticketed because it took so long to find him and bring him back to the car. I mentioned this to him, calmly asking that he respect my time and stay in a set location so that I don’t end up with a $25 ticket again. He looked at me with a good-natured shrug and said, “Well, that’s not much. You can afford that.”
Sonny, your parents paid me $140 a week and I was in college. I know you live in a $1.4 million house and your dad buys you an expensive new toy every Sunday, but with the money they’re forking over for your education someone ought to have taught you the value of a dollar by now. But honestly, he was a nice kid. They moved away and I hope he’s doing well.
10. The Smell of Success
I grew up in a very well-to-do suburb, and there was a family who had an extremely bizarre habit. They would buy cedar clothes hangers for their closets, but then once the cedar smell “wore off” after a month or so, they’d buy new ones and take the old ones to Goodwill. Apparently just lightly sanding them to refresh the scent was too much trouble.
11. Unreal Estate Problems
My brother works at a rehab center for the kids of wealthy parents. He’s always got stories, but the one that sticks with me the most was a kid who was in trouble with the law and doing rehab before his court appearances. You know, to look like a better person and hopefully the judge would go easier on him.
He was mopey one day and my brother asks him what’s wrong. The kid starts talking about how tough the whole experience has been for him, how it’s been so hard on his family that his parents had to sell his house to pay for his rehab. My brother felt sympathetic and says, “Damn, that sucks that your parents had to sell their house over this,” to which the rich kid corrected him, “No, they kept their house. They had to sell mine.”
12. Here’s a Tip: Don’t Be a Jerk
My dad and I worked for the owner of a big beverage company. The owner’s wife was yelling at my dad for a truly awful reason. Apparently, my dad tipped the garbage man $20. Meanwhile, I was carrying the $20,000-dollar lamp that she just purchased.
13. The Princesses and the Pauper
I knew these two girls, both were nice and fairly level-headed but also just raised too dang rich. One would take a taxi everywhere in town. It was a very safe, small college town with free campus buses, and she’d taxi across campus. She lived two blocks away from me and would take a taxi from her dorm to my house. Google Maps says it’s a full four-minute walk. She swore she just had a terrible sense of direction and couldn’t figure out where we lived, but you’d think after the first embarrassingly short taxi ride, she’d throw our address into Google Maps and just walk.
The other would regularly complain about people not knowing how to manage their money. It took a while to figure out, but eventually we figured out her cruel meaning: she only meant very poor people didn’t know how to invest their money in stocks and bonds. Then one day we were having a conversation where she revealed she didn’t think a house in Detroit in 2010 could possibly cost under $1 million. I told her I grew up in a nice $180,000 house and she thought I was dumb or lying. Shattered her world when I showed her my home on Zillow. When she graduated college, she complained about how much stuff cost all the time; it was nice seeing her learn the value of a dollar finally.
14. A Penny a Day Keeps Jerks Away
I went to high school with this insufferably rich kid. Family had a couch in their home’s elevator. And classical European sculpture (this was in the US). Kid talked down to/about the less fortunate on a regular basis. Once made fun of me for picking a coin up off the ground. Great guy.
15. Friends With BIG Benefits
My sister and I, both Latin American, befriended a Chinese girl in college. We always helped her in studying and with her English. Turns out her dad was some billionaire in China who owned a Chemical producing company. She drove an expensive Audi and for the longest, up until two years ago, I was freeloading off the Chegg account she opened up for me.
That account was paid for about three years. Whenever she’d invite us to go eat, the bills were super expensive, like $300+ for just three people, but she played it off like they were nothing. I had never once eaten a single meal over $40 per plate until we ate with her. She’d always take us to Starbucks, for food, and on a couple of occasions, she bought us books for school.
At one point, we went shopping with her. She wanted a laptop; she was gonna buy me one too, but I felt too guilty to accept it. The laptop was $3,000. I felt like it was too much. She was really cool and treated my sister like her sister. She was living alone and didn’t know many people. We were always friendly with classmates and that’s how she got to know us.
My sister and I are from low-income families. The money that was spent around her was ridiculous! Like $300-$400+ per lunch almost every day, that was around my weekly pay back then. Really miss her though, she was fun to be around with and always wanted to learn more about the US, always insisted we go out with her to movies, shopping or dining and teach her about our culture. Have not heard from her in three years. She went back to China and we never saw her on campus again.
16. 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.”
17. The Sweet Taste of Financial Security
When I was a supervisor for Starbucks, we had a regular who ordered the same (extra modified) Frappuccino every day, three times a day. She had to have it all the time and only liked getting them from a few stores. When she would go on road trips to her cabin, she would come in the night before and we would pre make a whole bunch of Frappuccino’s and not add ice or blend them.
This would be so she could blend them in her car on the way there and back. I did the math and realized the infuriating truth. This woman spent over $8,000 per year on this stuff. For the record, she was an heiress and only stayed home all day watching soap operas.
18. How Low Can You Go?
I knew this girl who made several blog posts about how she and her significant other were going to end up on the street because there was no places to live in their price range. I was concerned, until I learned the truth. She’s from a multimillion-dollar family. She meant is that there wasn’t anywhere available above the normal rent rate. But don’t worry, guys, they ended up in a top floor penthouse. Guess daddy came through. Neither of them work.
19. Too Rich to Use Your Noodle
Last year, I lived in university accommodations with a boy whose father was a high-ranking member of the Chinese government. Perhaps due to the fact that I was also Chinese, or as the result of the excess privileges lavished upon him from an early age, he immediately established me as his “best friend.” Then it got really disturbing. He started to stalk me to and from lectures, to the extent where I had to vary my routes every few days. I’m a girl.
Anyway, this chap was intelligent, however, had difficulties using common household appliances. He did not know how to use a microwave or a toaster. One day, at 10 pm, I heard a rapid knock on my door, which of course, was this guy. He had microwaved a bowl of ramen in a ceramic bowl and did not know how to get the bowl out because the ceramic was far too hot.
Sarcastically, I replied that he had better let it cool. Half an hour later, he knocked on my door again, and started whining, in the most piteous of voices, that now the bowl was cool enough to handle, his ramen had also turned cold.
20. 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.
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. The Not-So-Magnificent Seven
My dad, who is very wealthy and very stingy, once offered to get me out of a tough situation financially. I didn’t have a car and was really struggling to make ends meet. I was telling him about what was going on in my life, and he opens up his wallet and hands me all of it’ contents. It was seven dollars. He kept saying how “He’ll give me everything he has,” and hands me the $7. But that’s not the worst part.
He felt really proud doing it too.
23. 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.
24. Money Can’t Buy Friendship, But It Can Buy a Look the Other Way
The dude who relentlessly bullied me in school was also the son of one of the richest people in the city. One day, a teacher caught him with his hands around my throat, and I was pinned against a wall. We were both taken to the teachers’ meeting room, where it was explained to me that we should try and get along and that we should apologize to each other.
Did I mention his dad also built the flashy new cafeteria for the school that year? He was caught on numerous occasions with me in some state of distress, and every time they found ways to make it both our problem. His dad pumped a lot of money into that school. He also flew his friends on his private airline to Manchester United games so nobody stood up for me because they could lose their privileges.
My saving grace was a lot of his mates in early years of secondary school turned on him in the later years because he was such a jerk.
25. Don’t Hate the Player, Hate the Unplayed Games
Friend in college literally went to the local GameStop at midnight every Tuesday. He’d buy every new release for every console. We went over to his house one time that year and he had about 60ish games that were unopened. One time, we were walking around campus and he stopped by the ATM. He got his receipt and called his dad. Turns out his dad was worried his funds were running low, so he sent him $25,000 just to make sure he wasn’t going to starve.
26. Way to Throw a Dog a Bone
I once got asked to watch my buddy’s mom’s dog. Cute Pomeranian, super well behaved. I was stoked to watch the little dude. She messaged me and told me where the garage key was and that she left a couple of hundred dollars on the table for me. I did a double take. A couple hundred!? I showed up at noon and took the money and the dog and went into town.
Took him to the dog park, then the beach, and then we kicked it and napped for a couple of hours. Dropped him off around 6 pm. It was the easiest $200 I’ve ever made.
27. Hand-Me-Down Drivers?
I work in estate management as a side gig, and most of my clients are wealthy. It’s usually the kids who are out of touch. I once spent the most excruciating 10 minutes of my life trying to explain the concept of “used cars” to the college-aged daughter of one of my clients. She just could not grasp that some people buy cars that are not brand new.
She seemed to think that after a car get used for a while, it gets returned to the dealer and shipped off to a poor country. It was really bizarre; she was pre-med too.
28. Paying the Piper
I quit my job and set up my own competing business with my ex-employer after he failed to pay me for two months, claiming non-payment from the clients. He had a massive go at me after I confronted him with receipts from the clients to show payment and he accused me of making him look bad in front of them. He said that he didn’t owe me the money. I’ll never forget his words: “some people are bosses and some people are employees.”
I also warned a few of my ex co-workers to be careful and not let him rack up debt with them because of what he did to me. They are nice people with young families and don’t deserve to be taken advantage of, like he did to me. I took him to court to try to recoup the money he owed me for the work I completed. What do you know, the judge ruled in my favor for the full amount of just over £4,000. He then plays the victim card with everyone he knows and says that I made him and his family homeless despite the fact that he never paid me a penny of the money owed. £4,000 is like 5-6 months’ rent in a decent neighborhood in my city.
Honestly blows my mind every time I think about it.
29. 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.
30. With a Little Help From My Housekeeper
There was a kid at my high school. When he was 14, he had a learner’s permit, but his parents got him a Mercedes-Benz G-Class. Every day, he drove it to school and was determined to park it in the parking lot to show it off. So, he had his housekeeper drive to school with him and her son drove a car behind her to take her back home—which was only about two miles away from our school.
31. No Back-Up Plan?
Had a roommate in college who was pretty well off. I was pretty much putting myself through school and was almost always broke. One day we went by the ATM that dispensed in $5 increments (yeah, I made darn sure I knew where those were!) Anyway, turns out I had less than $5 in the bank, so looked at my buddy and said, “Well, looks like no beer for me tonight.”
He looked at me and said words that I will never forget: “Well, just take it out of your other account.” I just stared at him and asked what he meant. Turns out he legit thought that everybody had a second account their parents kept filled with “emergency” money! He did buy beer that night though, so he was a good guy. Just kinda clueless.
32. Too Big to See a Difference
I have an aunt and uncle who are both experienced aerospace engineers (retired military officers, now higher-ups at private contractors), so they make an obscene amount of money. You can always tell how much they’ve lost touch with the value of a dollar when you look at presents that they’ve bought. One time, years ago at Christmas, they made a huge, offensive mistake.
They bought my aunt a $600 iPod and my mom a $20 t-shirt. Still, they didn’t mean any insult; they just thought my mom would like a shirt better and that my aunt would like an iPod better, and they didn’t even look at the prices of them.
33. His Jokes—Like His Tab—Are Rich
I once went out with the ultra-wealthy parents of this girl I was dating, and they made a big deal of me ordering whatever I wanted and getting appetizers and dessert and drinks and everything. Once I put in like a $75 single-person order, her dad got me good. He just ordered two hot dogs and laughed at how expensive my meal was.
It was the most expensive lunch I had ever had at that point, and I really respect that man’s trollery. He had a much better sense of humor than his daughter. They were rich but at least they were funny.
34. You Can Take Home with You
I was born to a very wealthy family, though one who put a great emphasis on a strong work ethic. 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.
I was 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 something that makes my jaw drop. It only has 87 miles on it. It had just been purchased the day before in anticipation of a large group coming to visit.
35. Call It a Bad Harvest
Group of rich high school kids in Montana out driving around, drinking. Found two combines (large farm tractor thingies, worth about $250,000 each) out in a wheat field. Decided to have a demolition derby. Got caught. In the judge’s chambers with the farmer, who just wanted the damages reimbursed. The high-end family lawyers asked what the heck they were thinking when they did it.
The response: “Well, you can’t put a price on a good time.” Turns out that was the wrong answer…
36. The Minimum Effort
Several years ago, a job of mine led me to encounter a person who had come from a wealthy background, had a cushy job with a successful company, and rarely interacted with those below his socio-economic level. He decided to weigh in on a conversation about the economy I was having with some people. His opinions sounded so stereotypical that I was waiting for him to use the term “bootstraps” in a serious manner.
The reason I share this is that he went on to say that with minimum wage what it was, anyone could support themselves. He then revealed that he thought the minimum wage in the United States was $19.63 an hour. It took quite a bit of effort to convince him how wrong he was with that amount, and I respect him for accepting his mistake, but it blew the minds of everyone there that he could be so out-of-touch.
37. Wine and Dine Them
I became friends with a kid whose family was really well off. He was a really nice bloke, but a bit sheltered and university was the first time he really had any independence, but he had very little sense of what the value of a dollar really was since his folks got him what he usually wanted, compared to what normal people would spend.
There was one particular time he wanted us to eat at a restaurant, and he assured us “it’s really good!” so we all rocked up to this place and the price for main courses started at $40 to $60, which as poor Uni students we couldn’t afford. When he realized this, he was so embarrassed he got his folks to pay for it. He’s finally wised up a few years later once he got more independence away from his family and made his own money and remains one of the best blokes I know.
38. The Smoking Cash Stash
I sold hash to a business partner of my dad’s when I was in college. I had a variety, and it was the only drug he enjoyed. He obliquely asked me to bring it over to him—no discussion of what or how much. I biked over to his (very nice) place, and he had a coffee and a chat, and I simply handed it to him and was getting ready to leave, thinking maybe he’d have my dad pay me??
Nope, as I left there was an envelope on next to the rear entrance. It contained $500. For like $80 of hash. He would repeat this several times. He just needed a source he could trust and not raise eyebrows. When my dad passed, he helped manage the estate and we had an implicit mutual trust that made things go much easier.
39. 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.
40. A Drop in the Ocean
Back in high school we were doing one of those ice breakers where we passed a beach ball around and whoever caught it had to answer the question their thumb landed on. Well, this kid who has proclaimed being rich numerous times before talking about his parents owning a known pizza place and how he drives an expensive sports car caught the ball.
His question was, “If you won a million dollars what would you do with it?” His response made my blood boil. It was something along the lines of “A million dollars wouldn’t make any difference in my life.”
41. Shop ‘Til You Drop (Your Innocence)
In college, as I was making dinner one night, my wealthy roommate expressed surprise that you could get vegetables in a can—like totally in shock at the idea of canned vegetables. It turns out that in his house the cook simply went down to the market every afternoon to pick up fresh veggies, and he’d never known it could be done any other way.
This was not a post about the virtues of canned vegetables, but about the idea of someone so isolated by money that they had never been in a grocery store.
42. Cash and Crashed
A group of rich kids who went to high school with me got super drunk at a party and then drove home and crashed the car. Only one of the four of them got in any trouble (she ended up getting maybe 40 hours of community service). Then this girl was complaining about how her parents wouldn’t buy her a brand new, fairly expensive car for her birthday until she got the community service done.
43. That’s a Wrap!
I’m wicked late to this but back when I was a cashier at Chipotle, I had a woman misunderstand the price of a burrito. She heard me say “that’ll be seven-twenty-eight” and without any hesitation, counted out eight $100 bills from a wad of cash that must have been several thousand dollars. We had a good laugh when she realized her mistake. She was carrying a suitcase and had a thick accent, so I think it may have been her first cash transaction in the US.
She was just so rich that it didn’t occur to her that $800 was a load of money to spend on a burrito.
44. 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.
45. Swipe Your Fears Away
A friend of mine was dating a super-wealthy girl in college. Not sure how they got together, it was some internship thing or something. He grew up pretty poor, and he told me a story about how they were at Wal-Mart and he was considering buying a pair of flip-flops, but they were like $10 and he wasn’t so sure it was something he could afford at the time.
Apparently, she said to him “What do you mean, you don’t know if you should get them? Whenever I want new clothes, I just ask my daddy for the money card.” She literally used the phrase “The Money Card,” as if it was some weird artifact that magically made all clothes free for her (which, I guess it kinda did). He also told me she felt the need to take a full shower every time she pooped, which… I mean, that’s a different thing, but still funny.
46. Some Heroes Use Credit
I worked at the concessions stand at a movie theatre, and it was opening weekend for a large Marvel movie; the line was super long to get popcorn. This rich millionaire dude from India walked up to me and handed me his AMEX black card and waved a hand over the entire line of customers and said, “WHATEVER THEY WANT, MY FRIEND,” and plopped it down hard on the glass counter.
I’m just like “…Are you sure?” Him: “WHAT UH EVA THEY UH WANT!” with a huge smile on his face. He waited as the entire line ordered tons of food, entire combos, large everything, extra candy. I was like “You total is uh… $10,718.62” and I swiped the card and it said, “Transaction complete,” and he said, “Thank you my friend” and he went to watch his movie having fed everybody in line.
Absolutely unreal moment. And no, I didn’t get a tip or anything but now I have a cool story to tell. Complete strangers with just an unlimited budget to spend on movie snacks and drinks thanks to this man they didn’t even know.
47. 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.
48. 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.
49. 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.
50. Small Business, Big Problems
Small business. 20 employees +/-. Boss made a big speech about austerity measures and no raises this year. A week and a half later he takes “jerk” to the next level. He drives up in a brand new Silverado with all the bells and whistles. Expensed to the business of course. He would hate to have to pay taxes on those profits.
One of the less subtle members of the staff got her revenge. She took a literal dump in front of his office door.
51. 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. 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.
52. The Grass is Less Relatable on the Other Side
I grew up absolutely dirt poor. I’m 28 and I often have to help my parents pay their bills still. But my wife comes from money. The effect on her is minimal as her parents were self-made and taught her to work for everything she has. Sure, if we were destitute, they would bail us out, but they aren’t handing out gifts. But because of this she ended up going to a really nice school in “that part of town” and all of her friends come from money. Some of it very old money. Their parents bought their first cars, put them through college where they never had to work, paid for their weddings, and put down payments on their houses.
They are all really awesome people and I love having them in my life, but sometimes they just don’t get it. Naw man, we can’t go out to Europe with you guys for two weeks because we gotta work, and just can’t afford it, our mortgage is due this week. No, we can’t really afford to eat at that place the third time this week, our dog had an emergency visit to the vet.
53. Your Ingratitude is My Pleasure
When I got out of the Navy, I decided to use my GI bill at one of the Penn State satellites. I was sitting in the cafeteria drinking coffee and typing up a paper when a girl sits down across from me and opens her backpack. She pulls out a sandwich bag and looks at it in disgust then looks me dead in the eye and says, “I don’t even know why I bother; my mother never cuts off the crust.” I let out one of those high-pitched short laughs, like, is this girl for real?
Oblivious to the tone of it she says, “I know right” then asks me if I want it. I looked around thinking I was getting pranked or something ’cause this stuff is too stereotypical to be real, and I just assumed I was being filmed. She shook it at me and gave me a “Well?” look. So, I said screw it and took the sandwich. She then pulled out her student ID card and bought a ton of French fries. That sandwich was awesome; I think the bread was homemade and it was stacked like a Dagwood. It had all kinds of expensive looking meats and Dijon mustard, serious gourmet stuff. I know this girl’s mother will never see this, but I just wanna say someone appreciated that sandwich.
54. At Least He Learned the Value of a Dollar (or 20,000)
Worked with this kid who was a good kid, but completely disconnected from the financial realities of most people. He’d just moved out west from another state and was trying to get on like a “normal” adult. He went to buy a new car and was shocked that they couldn’t just bill his dad for it, because they didn’t know him.
He ordered a bottle of wine at a restaurant and the sommelier said “Certainly, sir.” Then the sommelier whispered, “Just for your knowledge, sir, the bottle is $700.” He looked straight at him and asked, “Is that a lot?” The employee honestly didn’t know how to answer. He was a good kid, and he got a lot better, but he just didn’t know. Once he casually told his mom he needed some help with bills, and she deposited $20,000 into his account.
55. I’ll Drink to That!
The first time I walked into my rich girlfriend’s parents’ house, someone was asked if they wanted water. I’ll never forget their response. They asked, “What kind?”
56. Fantasy Island
My friend is a middle school teacher in a pretty wealthy area. The kids got back from summer break one year and he asked them how their vacations were. One kid said, “It was lame. We spent two weeks on our private island. It’s so boring there!” Entitled? Yes—but at that age, you kind of just have to feel sorry for the kid. They don’t know any better.
57. The School of Not-So-Hard Knocks
When I was in boarding school, one of my co-boarders handed me some mail saying, do you notice anything special about this envelope?” When I checked it out, my jaw dropped. His his face was on the stamp… He was royalty. A rich kid from Taiwan was also attending same boarding school. My advent calendar had little chocolates, his had a remote-control car, Sega Game Gear, etc. etc… Another teenager arguing on the phone to his grandfather that he didn’t want a Porsche, he wanted the Ferrari….
58. The Mother of All Insurance
I need to say first, off the bat, that this is about my best friend, and she is the best person I know; i.e. not normally “rich kid” or anything. I was complaining about how I was short on money one month (just couldn’t go out to eat) because I had to pay rent and pay for tag renewal all in the same paycheck. She looked at me, super seriously, and was like, “Don’t worry they send you those in the mail for free!”
After a long discussion she learned that in fact, her mom had been paying for her new tags every year.
59. Money Please!
I work for a dentist, and her son is a spoiled brat. He was at the office one day because she had to bring him to an appointment later that day. He got bored and went out wandering around some of the local shops. He came back a little while later and without any preamble walked up to her and said, “Give me $80.” She asked him what it was for, and he just repeated himself and she gave it to him.
So, the kid is 19 years old; he was 17 at the time of this incident. The father is in the picture, but my boss (the dentist) is the main breadwinner and disciplinarian of the family. The husband is more like another child and just works here and there and lives off her money. She tries to act tough and instil certain morals and values in her kids, but then turns around and caves to all of their demands.
For example, her twin daughters are utter nightmares. They are going to university next year and instead of staying in a dorm they demanded a two-bedroom, two-bathroom apartment. They refused to share a bedroom or even a bathroom. At first, she told them absolutely not; but they whined and complained, and she caved. This will be a two-bed, two-bath apartment in Toronto by the way where rent prices are through the roof. My boss is very much about appearances and from a young age got her rich kids accustomed to a privileged lifestyle. She created monsters.
Yes, they are totally like Jean Ralphio and Mona Lisa Saperstein.
60. She’s Come a Long Way
My roommate during my freshman year of college was a super sweet girl, but she grew up insanely wealthy. She was so entitled, yet clueless as to how real-life worked for most people. To me, it wasn’t so annoying as much as it was entertaining. One time, she asked me to go to the ATM with her for a truly ridiculous reason: she honestly didn’t know how it worked.
She needed about $300 in cash to buy football tickets for her family. The withdrawal was declined because she didn’t have $300 in her account. She looked at me and said, “Am I poor?” with the most heartbreaking face ever. It turns out she thought that her family’s money was all in some big account that they all had access to, because she’d always had a credit card that had never been declined.
We had a lesson about personal finance and just the way that banks operate in general after that. She ended up being a pretty good roommate—at least after she learned that we did not have a maid and accepted the fact that she had to clean up after herself. She wrote me a sweet note when we moved out thanking me for my patience with her. She was entitled and spoiled, but ended up being a lot less spoiled by the end of the year. It was nice to see her become more self-aware and change for the better.
61. Work to Live, Live to Complain
Had a friend tell me that he was “done dealing with [mutual friend] because they had given up on themselves”.
What they had actually done was worked for a year before starting grad school because their father isn’t a millionaire, who has paid all their bills into their thirties while they played around and had fun with hobby-jobs without having to worry about financial security. They didn’t understand how much life actually costs when you pay your own bills and thought less of people for working to pay their bills.
62. Wage Wars
The president of my company asked me the most infuriating question I have ever heard. He sauntered up to me and asked if I thought I could live on $100 per day. I told him I did every single day. I was probably making $13-$14 an hour at the time.
63. Rich Enough to Cheap Out
“I could absolutely survive on my own; my parents just pay for my food and house, but I pay for everything else. If I got a job, I could pay for my food and house too.” Said at 18, in the middle of a discussion between two middle-class peers who were talking about saving money because they had to pay for their own college and living expenses. About five minutes prior to this conversation, both peers had ordered the cheap dinner options and declined a shopping trip later that night, while rich-girl was talking nonstop about buying the best/most expensive souvenirs for her friends.
Once tried working a regular-person-retail-job and quit within a couple weeks as it “just wasn’t right and I didn’t like it” (read: had actual responsibilities for the first time).
Moved cross-country for an eight-month education course, where her parents pay food, rent, and school. They also gave her a debit card which replenishes up to $500 when it hits $50… she still posts Snapchats with captions of “that broke person life” over pictures of her getting Starbucks every day and insists she could survive on her own.
Constantly suggests the most expensive options for meals, activities, etc., and tacks on things like “We can just split the bill, I know you’re saving but it’s just [amount at least $50], you’ll be fine right?” Then gets upset when people can’t afford to spend time with her, or when someone dares to suggest that she helps cover costs.
64. The Road Less Traveled
When I delivered pizza to a wealthy area, I once had the following incident occur. I got to a big and fancy house, rang the doorbell, and waited around. No one answered. I then knocked just in case the doorbell was broken. I still got no answer. I called the house on the phone number they had ordered from; no answer there either.
As I’m about to call my boss and tell him what’s going on, my phone rings and it’s some lady who reveals herself to be the mother of the kid who had ordered the pizza. She said that her son would be right out in just a moment. So, I’m waiting for another five minutes, and there is still no one showing up. Then, all of a sudden, flying down the street and into the driveway comes a Mercedes G-Class.
A middle-aged woman frantically gets out, pays me—with no tip—and apologizes for the fact that she couldn’t get her son to “come up from the basement to get the door, because he’s watching a movie.” I couldn’t believe it. This woman’s son ordered a pizza, but was too lazy to pause the movie he was watching to come up the staircase and answer the door to get it.
So, rather than that, he phoned his mother and made her drive all the way home to get it for him—and this idiot woman had absolutely no problem complying with that ridiculous demand! I hope the little brat enjoyed his pizza and breadsticks. Good luck to him in the future—he’ll be needing a lot of it some day if that’s his attitude towards life.
65. We Have Always Lived in the Castle
Friend got a theater with an arcade built over their family’s 12-car garage. Parents didn’t want the five-year-old sister to be jealous, so they hired an architect to design and build her a fully functioning playhouse with a bathroom, bedroom, and air conditioning. Just the tip of the iceberg with this family though.
The wife bought a popular fast food franchise unavailable in our area because she didn’t like having to drive 30 minutes to get what she wanted. Their Bentley had a fur floor. At the millennium, the father was into tattoos and regularly spend tens of thousands to fly the best tattoo artists in the world in from Japan and LA to work on his “Yakuza style” sash tattoo. I could go on and on.
But the number one thing that I think might qualify one in the family for “rich kid syndrome” is that the father, who inherited his family business from his father, sold the business overseas in the late 80s. The company was the only reason the town had to exist. Ever since, the community has been recognized as the most depressed in the state, and the schools unequivocally the worst.
66. 911, How Much is Your Emergency?
I once had a mom ask if I could open up the back of our ambulance so her kid could see what was inside since he “wanted to be a firefighter” (I’m a medic, not a firefighter). I agree as long as he doesn’t touch anything. Of course, the second the doors open the kid hops in and goes straight for our expensive monitor. I tell him no, that’s it’s dangerous and could break, to which he starts screaming “I don’t care, my mom will buy it,” and the mom says “It’s fine, just let him play with it, if it breaks I’ll replace it.”
I had to physically pick him up and carry him out of the ambulance since she didn’t even try to control him. While this is happening, we get paged out for a call and this witch suggests that she could pay double our hourly wage if we stay for a few more minutes so her little brat could explore/destroy more of our equipment! Screw outta here with that nonsense lady. You’re willing to delay an ambulance so you won’t have to deal with precious little Joey’s tantrum? Unbelievable.
67. Flying Solo
My roommate refused to go with his family for spring break for a truly horrifying reason. There wasn’t a flight with first class seats and only business class was available. He ended up taking a connecting flight that did have first class available while the rest of his family just took business on the direct flight.
68. The Family Retainer
It took me a while to get used to my girlfriend’s lifestyle. I grew up in a very working-class family with both my parents working full time just for us to stay afloat. Went around my girlfriend’s house and saw a lady making food in the kitchen, “You must be Mrs. (Surname),” trying to be really polite and introduce myself to her family. That was actually their maid, awkward.
Luckily, they’re all really down to earth and stuff cause turns out her parents were basically homeless and living out of a storage space when they were my age, but her parents started up a little business that actually became successful enough to support them, and then just kept growing.
69. A Steak in the Matter
I was a waiter at a small restaurant for a number of years. Our worst incident involved a group of six to eight guys, all in their late teens or early twenties. They went all out, ordering expensive drinks and cocktails. Everyone ordered a steak as their entree. One guy, who seemed suspicious to me right from the start, ordered his steak medium well, with every sauce available.
They stayed for over two hours, racking up the bar tab after they cleaned off their plates. Some of them were even literally licking their plates at one point. Well, they eventually called for the bill and I dutifully brought it over to their table. The suspicious guy pulled me aside and informed me that he would not be paying for his steak.
Apparently, in his opinion, the garlic butter was frozen, rendering the steak that he had happily wolfed down “completely inedible.” I looked him dead in the eye and said, “Dude, the garlic butter doesn’t even stay in the freezer, there’s no way it could’ve been frozen.” The guy took offence to this and demanded to see my manager.
He demanded that his inedible steak be taken off the bill. The guy then explained that he goes to some of the best steakhouses in the city, and knows a lousy steak when he sees one. The manager then looks at our customer, looks over at me, and turns back to the customer before delivering the perfect burn: “What kind of freaking moron orders all three sauces on one steak?”
70. Doesn’t Sound Like a Nice Guy, But Okay…
I have a rich kid in my MBA cohort that outsources his homework and projects to India. He whined and moaned when one of our professors gave him a “C” when he only showed up to two classes after “he (dad)” donated $10,000 to school. Overall nice guy but doesn’t really have a clue.
71. 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.
72. Second-Class Flying, Third-Class People
I went to middle/elementary school with some very wealthy people. In fifth grade, we did an exchange trip type of thing with some kids in Canada. On the flight over there, one of my classmates said, “Wow, this is crazy. I’ve only ever flown first-class before!” Later, in eighth grade, I was at that same rich kid’s house (an absolute mansion on top of a hill) and he and a girl (who had been dropped off in her dad’s “newer” Ferrari) started comparing the merits of their relative in-home movie theaters. Like, not just a living room with a cool A/V setup, but full-on movie theaters with rows of seats that could seat about 50 people.
My family wasn’t poor, but that was when I realized we weren’t rich either.
73. Fortune with Extra Cheese
I deliver pizza in a VERY rich area. I’m talking seeing Rolls Royces and supercars on a daily basis kind of rich. My manager told me a story of someone that used to work there. This guy would deliver pizzas in a brand-new BMW M3 and just put absolutely no effort into his job (delivering pizza isn’t hard).
Apparently. this guy only had a job because his parents wouldn’t pay his allowance if he didn’t work. How much was his allowance? $5,000 a month. This guy was making $60,000 a year to deliver pizza part time.
74. Maid to Be Impressed
I brought my rich college roommate to my mom’s house for Thanksgiving because he lived in a different state, and I only lived 15 mins from campus. I gave him a quick tour of the house, and he was astonished by how clean it all was (my mom’s a neat freak and keeps a very clean house). He then said something that made my mom laugh harder than I’ve ever seen. He turned to her and said, in such a genuine voice, “Wow you guys must have a really good maid service.”
75. 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 taking “rich lady nonsense” to the next level. They 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 just did what they did best. They used their money to get out of the problem: they simply bought their maids memberships!
76. Sticking Around
Went to college with a totally chill dude who was apparently rich as heck. He was on our college golf team and enjoyed destroying a club if he hit a bad shot. He wasn’t even angry; it was just like a reflex to go Bo Jackson over his knee or whatever.
I asked him how he keeps playing, and he basically said that at the end of every round he just bought new clubs for the next round. He showed me in the trunk of his car how he had like five boxes of irons and always took the plastic off a new driver for every round I saw him play (and he played every day at least 18 if not 36 holes). He said it wasn’t even a rounding error in his dad’s credit card…
77. 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.
78. Let It Snow
One of the kids in my grade brought bags of drugs to senior prom. And it wasn’t just his parents who let him. Oh no. This thing went right to the top. Mom and dad must have bribed the police because they were in on it too. Now I believe he’s in an engineering program at Yale.
79. 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.”
80. 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.
81. Why Not Buy the Neighborhood at This Point?
My boss bought her kids a $2,000,000 house to live in while they went to college. My boss also paid for their college. So of course, they move out of the$2,000,000 house five months later because they want to be independent. Oh yeah, and expect mommy and daddy to pay for their rent, utilities, college, cars, vacations to see friends in different states…etc.
82. 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!”
83. More Money, More Mental Problems
Had a friend in high school whose dad was uninvolved. He was raised middle class like me and lived with his mom and stepdad. After high school, he worked towards becoming an electrician and was saving for his first apartment. His dad eventually came around when he was right out of high school and started giving him money here and there when he needed it. His dad owned a large company on the east coast and was a multi-millionaire.
Soon his dad convinced him to quit trade work and gave him a job at his business. Shortly after, he was promoted to a managerial position he wasn’t qualified for and paid way too much. Little did he know, this was the biggest mistake of his life. He’d get drunk while on conference calls and nobody questioned him since he was the boss’s son.
His dad bought him his first home (almost half a million dollars) and multiple cars. He took up horse racing and, quickly, we had nothing in common. Gone we’re the days of dumb teenage stuff, going fishing, hiking and playing video games together. He quickly found a girlfriend whose dad was also a multi-millionaire. She was 30 and still putting everything on daddy’s credit card.
After his girlfriend and him broke up, she revealed the awful truth. My friend was actually severely depressed and almost drove his car off a bridge multiple times. Deep down, he was having issues with wanting to live up to his dad’s lifestyle and standards but losing his old friends and life. It’s too bad. I haven’t seen him in probably four years now. We tried to reconnect a few times, but it just doesn’t work anymore.
84. Would’ve Been Loaf to Deny Her
I worked at a very expensive and exclusive country club, the type you’d see the Bluths at. One of the members drove her golf cart over from her house. She said the help had forgotten to buy a loaf of bread, and she wanted to buy one from our kitchen. I told her that we couldn’t sell her a loaf of bread, so she asked how many sandwiches a loaf of bread can make.
I ended up selling her 10 sandwiches with nothing on it at seven dollars a piece.
85. A Phone is Like a Fish: Catch and Release
I taught for six years at a school with extremely rich kids (the professional athletes in my city would live in this district and their kids would go here, and lots of other wealthy people). I taught seventh grade. One of my students had the iPhone 6. He wanted the newest phone at the time, the 6S which had come out that week—so this was probably late September. During the bus call, he was whining about his parents telling him that he had to wait until Christmas to get a new phone.
What did he decide to do? He chucked his phone at the cinderblock wall in the hallway from my classroom. It broke his screen, and possibly his phone. He had the iPhone 6 the next day.
86. 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).
87. Must-See-TV Means Must See
15-year-old girl insisted that the family’s flights to a pacific island get pushed back a day so she wouldn’t miss an episode of her favorite TV program. They went a day late on vacation. This was in 1998 when streaming wasn’t an option. As some of you have pointed out she could have recorded it, but obviously that wasn’t an option for such a princess. ginger-ghost
88. 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.
89. Daddy Warbucks Comes Back with a Vengeance
I worked as a bouncer at a high-end night club. The worst 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 and his reaction is truly epic.
He’s obviously ashamed and furious at this brat of a kid. He 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.
Definitely the most satisfying experience I had working at that club.
90. Money Can’t Buy Class
Attended an international high school in Ho Chi Minh City, where a lot of new-wave millionaire’s kids live. The school was ridiculous, a third of the kids were expats (perfectly lovely kids), a third were local Vietnamese kids whose parents were working their BUTTS off to send them to a private school, and the other third were these rich kids.
They wouldn’t ever hesitate to show off their mummy and daddy’s wealth. They’d pull up to school in Lamborghinis, Ferraris etc. etc. and if their Rolls Royce didn’t come on time to pick them up after school it would be a straight phone call to their other driver to COME PICK ME UP RIGHT NOW.
They’d be such jerks 24/7 to the non-rich locals (classist kids), and constantly just bringing up the most trivial things and complaining about them. I’m literally not exaggerating here when I say this: e.g., my maid bought me the WRONG LV bag! I TOLD HER it was the TAN BROWN one not the LIGHT BROWN one! Ugh I can’t believe it—now we have to send her on the jet to Shanghai to get it.
They all paid and used family connections to get into Harvard, Stanford, UPenn etc. etc., and even now constantly complain on Facebook and Instagram about how bad their residence hall food was so they just hired some freaking personal chef or something. Mind you, these kids were the DUMBEST bunch I’ve ever seen—one of them literally was clueless about the most basic facts but still got into business management.
Despised the lot of them. Glad I’m in Europe, far away from most of them.
Man, I’m clearly not entirely over it.
91. 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. The next day, we all got an utterly heinous memo. 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.
92. Size Matters to the Little One
I was nannying for a wealthy family in the upper east side of Manhattan when I got engaged to my now-husband. Boy, age eight or nine, thought my ring was super cool and unique because he “never saw one that small before.” Thanks, kid.
93. 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!
94. 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.
95. 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?”