Wealthy Kids
I grew up surrounded by wealthy kids and stayed in touch with a few of them. One of them, whose father owned the most powerful law firm in town, once opened up to me about a moment that changed his life. After being arrested for the second time, he called his dad from jail expecting help. Instead, his father simply said, “Sorry to hear that. Good luck,” and hung up.
That call hit him hard. Being walked back to his cell made him realize something: the safety net he always assumed was there had vanished. That moment forced him to rethink everything. He never imagined his father his lifelong safety blanket would step away. But not every rich kid faces consequences the same way. The boy in the next story? His parents had a very different way of teaching lessons and they were quicker on their feet.
Partied Hard
I went to school with a wealthy kid who partied hard when he left for college. Every night, he was out, enjoying the freedom and ignoring his studies. Eventually, his grades took a nosedive, and it didn’t take long for his parents to catch on.
One Saturday morning, they showed up without warning, took the spare key to his car, and drove off with it. No arguments just swift consequences. He learned the hard way that actions have repercussions. And just like him, the next person in this story was served a healthy dose of reality.
Through His Twenties
I have a distant relative who blew through his twenties living off a hefty annual allowance of $100-120k from his extremely wealthy father. Every year, he took lavish trips to places like Bali, Thailand, Europe, and Oktoberfest, enjoying a nonstop party lifestyle.
At 32, he settled in a fancy ski resort in the U.S. and launched a business with his gold-digging fiancée. One day, while transferring money to his American bank account, he was shocked to find only a few thousand dollars there. Furious, he confronted the bank, only to learn his father had quietly cut him off without warning. He had never noticed until that moment, thinking he was untouchable until reality hit hard.
Back In College
Back in college, there was this son of a wealthy NFL star living in my dorm. He acted like he was above everyone else just because of his family’s money. Unfortunately, he used that privilege to coerce freshman girls into degrading acts while secretly filming them. The worst part was how casually he shared those videos with his friends the next day.
Luckily, one of his friends couldn’t stand it and reported him to the RA, who then involved campus police and eventually the real police, especially since some victims were underage. One night, we all watched as police flooded the parking lot, arrested him, and confiscated the evidence from his room. What happened next made me realize how some people manage to cope with the harsh realities of everyday life.
During Freshman
During my freshman year of college, my roommate came from an extremely wealthy family in the Middle East that owned an oil company. He was struggling with something most of us took for granted: cooking for himself. Used to having meals prepared for him, he found the simple task of making breakfast surprisingly difficult.
One morning, I found him in the kitchen trying to eat eggs and toast he had cooked. He asked me how to fry eggs properly because his were unusually crunchy. Turns out, he’d cracked the eggs into the pan with the shells still on! I couldn’t help but laugh, even though I felt bad for him. It was clear this was his first real taste of independence—learning the hard way that money can’t solve every problem.
A Large Sum Of Money
A university was approached with a large sum of money from parents eager to have their son admitted as an art major. However, the administration and faculty declined the offer because the student did not meet the academic requirements and showed little talent for art. Despite the family’s belief that money could secure his enrollment and degree, the university stood firm.
The young man was stunned to receive a rejection letter. Meanwhile, another student believed that his grandfather’s wealth could help him simply pass high school. These situations highlight the mistaken idea that money alone can replace merit and effort in education.
Never Needed To Pay Attention
There was this boy in my high school who always boasted that he never needed to pay attention in class because his grandfather was the Vice President of the company supplying cardboard for General Mills cereal boxes. He genuinely believed his family connections would guarantee his success without effort.
Last I checked, five years after graduation, he was still working at Best Buy the same job he had during school. On a different note, another guy I knew once threw a full-blown tantrum just because his credit cards weren’t working. These moments always stood out as reminders that reality doesn’t always match our expectations or attitudes.
Hired To Help
A few years back, a couple from Woodside, CA, hired me to help their difficult 18-year-old son face the realities of adulthood something his parents had struggled to teach him. The first step was to take away his unlimited platinum credit cards, which led to an intense multi-day tantrum. When he asked how he’d get money, I simply told him to get a job. Despite his threats that his parents would fire me, they stood firm.
Over time, he realized his parents had set clear boundaries, requiring him to pay bills, rent, and taxes. To buy himself time, he chose to attend college for four years. While he’s still somewhat obnoxious, he now holds a job and is pursuing an education. Next up: a story about a spoiled liar who loved spending other people’s money.
Spoiled
I had a college roommate whose parents covered a trip we were planning. He told them the trip cost $400 more than it actually did, just so he could afford a pair of pricey headphones for himself. His parents always spoiled him, even giving him one of their credit cards, which he used daily for food orders and frequent $50 purchases.
Eventually, his parents found out about the lie. They still paid for the trip but immediately revoked his credit card privileges afterward. Without the card, he acted like life was suddenly tough, but over time, he adjusted and became much less entitled. Although he’d never admit it, the experience had a positive effect on his attitude. The next person in line definitely had some lessons to learn before getting their own expensive car.
Back In High School
Back in high school, a guy flaunted his brand-new Chevy Camaro while I was driving an old 1980s Pontiac Phoenix with a straight-six engine. He never missed a chance to brag about how much better his car was compared to mine. One day, at a red light, my friends and I were stopped when he, clearly feeling confident, challenged us to a race.
He revved his engine loudly and tried to do a burnout on the dry road. After some effort, he managed a small burnout with a bit of smoke, but as soon as his tires gripped, he lost control and crashed into the car of the wife of one of the few police officers in our small town. Needless to say, things didn’t go as he planned, and I can only imagine how embarrassed he must have felt afterward.
It’s Not What Is Supposed To Happen In Vegas
While working in a casino here in Las Vegas, a herd of girls came to my window, & one proceeded to tell me about her great birthday party itinerary that her dad had paid for. For her 18th birthday. With no adults in the party. Just a bunch of teenage 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.
They start yelling & screaming at me. I calmly call security – and security tells them they can either “go play in the arcade” or leave & try to find a hotel off the Strip that will take them in w/out being 21. The anger turns to tears. The security guard is unmoved. How embarrassing. The girl in the next story surely needs a reality check before she goes out to get coffee.
Living In A Dream World
I was at a Starbucks, and the girl in front of me apparently thought people gave her parents free drinks and such for her all these years.
The cashier told her the total, and she said, “Wait, I don’t get it for free?” She never realized her parents swiping their cards all those years were paying for her things, I guess. The spoiled brat in the next story will prove that being rich just isn’t enough these days.
Everything Is Not Enough
When I was a teenager, my sister and I saw through our windows that there were two guys getting into her car. We ran downstairs as fast as possible and caught them in the act of stealing it. One managed to run away, but the other one froze and didn’t run away. He couldn’t have been much older than me. My sister called the cops, and the kid kept looking at us and trying to find a way to escape. My sister said, “Run if you want. My brother will catch you.” The cops came, and so did his parents. His mom drove an amazing car, and the lady looked furious and sad. She was dressed really nicely and looked like she was pretty successful.
As soon as she got out, she began yelling, “Why?! We give you everything! You have everything! Why would you try and steal?! Don’t we give you enough?!” The kid just seemed to shrink and get smaller. I hope he turned his life around and began to be around better people. The guy in the next story thought he could do whatever he wanted and not face the consequences of his actions.
Cashing Checks
During my freshman year of college, the guy across the hall from me is a spoiled rich kid from a big southern city. Old money, clearly. A couple of weeks into the second semester, he and a buddy found a checkbook on the sidewalk. He stupidly decided to write themselves a check and cash it in the bank that the account is in. The teller immediately called the cops, and they both got arrested.
We talked the night he got arrested, 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 he got expelled. I guess daddy didn’t take care of it. The poor little rich girl in the next story thought everyone owned a horse.
The Wake-Up Call
I went to a very rich, predominantly white Catholic high school. One moment I remember was the wind absolutely being taken out of a girl's sails when I explained to her why our school dominated the area’s skiing, golf, and equestrian competitions but never anything else.
For a lot of kids in that school, the moment they learned they were rich was the moment they learned that most girls don’t have their own horses growing up. Another kid who needs a reality check is in the next story.
Tow Away
A local rich kid had his SUV parked in a no-parking area at a club. A tow truck shows up to tow it away, and the kid goes ballistic, “do you know who my dad is” etc, to the driver.
After a minute or two of this, the passenger gets out of the tow truck and is a 250 lb powerlifter. The biker “politely” tells him it doesn’t matter who he thinks his family is, and the SUV is towed away. The rich girl in the next story just couldn’t understand why some of us have to count our pennies.
Do The Math
I knew one girl who apparently couldn’t fathom how people live on a budget. We used to hang out a lot at her insistence, but she liked to eat at expensive places, whereas I’d have no issue having my meals somewhere cheaper. However, she kept pouting and insisting I stay. I said I couldn’t unless she wanted to spot me. She didn’t.
I then walked her through the math and showed her that the cost of my meals with her every day totaled my entire wage for the month. She didn’t stop pouting, but from then on, I could eat by myself in peace. The entitled guy in the next story got taught a lesson he wouldn’t soon forget.
Grand Theft Auto
A guy from my robotics group had his entire life handed to him. His dad was stupidly rich because he bought shares in an oil field that turned out to have 40x the expected yield (making his $100,000 investment become around 3 million) then he dumped that into real estate rentals. He decided it would be fun to go on a school trip in Philly and act like a rich jerk to everybody. Soon after, his $90k SUV got stolen.
The best part? He didn’t have insurance on it yet because he “can just buy the other person’s car if there’s an accident.” His dad flipped out over it and cut his allowance to $200 a month, and forced him to drive a beater till he saved up his own money. The next story proves that you actually have to put in the work to finish university.
No Pain, No Gain
One of my college roommates was very rich growing up. I didn’t realize just how rich until I had to explain to her what a coupon was in very extensive detail. On multiple occasions, she bragged that she wasn’t even interested in her major (philosophy) or college in general, but she was at uni because her parents required her to get a degree, any degree, in order to get access to her trust fund. I don’t remember ever seeing her go to class, and she eventually got expelled sophomore year over academic dishonesty. I guess this was the last straw for her parents because they cut her off pretty soon after that.
This actually served as a wake-up call. She somehow managed to get a public health degree at a different school in spite of the academic dishonesty listed on her transcript. She’s doing pretty well for herself these days. We’ve kept in touch, and last we talked, she was considering grad school. The guy in the next story learned the hard way that college was not a year-long party.
The College Nightmare
This rich scummy injury lawyer’s kid was in my class in high school. He goes to college (a mid-size school in the Midwest) and gets plastered (his parents bought him and his friends' booze since freshman year, so nothing new), and RA says he has to write him up for drinking in the dorms.
He punches two RAs, then gets cops called on him and knocks a cop’s tooth out. Long story short, his parents have to drive back 6-7 hours after one day to get him, and he’s not even allowed to leave the state until his hearing. Last I heard, he was working at a fast food establishment. The rich kid in the next story learned that you can’t get everything you want just handed to you on a silver platter.
The Cowboy
This local business owner put his son through college and more. When the kid graduated with multiple degrees, the dad decides to retire and turn over the business to his son.
Son brings college cronies on board, has management all wear white cowboy hats and drive white pickups, and begins revamping the business. Dad comes out of retirement pronto and gets rid of his son and cronies. Years later, bankrolls son’s run for state rep. The son lost. Dad dies and leaves the business to his daughter. The next kid would learn a good lesson in being thankful for what you have.
Ungrateful
I knew a rich kid whose parents bought him a car, and he treated it like absolute garbage. Purposely driving it really hard and generally abusing it, confident in the notion that his parents would buy him the one he wanted after he destroyed the one they got him.
Well, they didn’t buy him another one, ever. He rode the city bus and bummed rides off of friends after that. He was the most entitled person I’d ever met. If he was over at your house, he would just help himself to whatever was in the fridge like it was some sort of paid buffet. Sometimes it’s just better to tell the truth, as this guy would learn in the next story.
Not Admitting Guilt
I saw a college guy with a ridiculously expensive car (can’t remember the model) rear-end this woman who drove an absolute beater. Her car was definitely totaled, and his car wasn’t looking that hot, either. He got out and started screaming at this woman. She was in tears. He kept telling her that she was going to pay for this. When the cops came, I saw each of them give their statements. After that, me and ten people came forward and gave our witness statements.
It sounded like each and every one of us put complete fault on him (which was the truth). When the cops went back to him, I saw his face just sink. He probably told them it was her fault and just found out that two handfuls of people just confirmed that he’s full of lies. I’ve never seen that many witnesses stick around for a simple traffic accident. I think the other people felt the same way I did: that kid was a jerk and should be punished for what he did. The rich girl in the next story will learn that being mean doesn’t always get you what you want.
The Mean Girl
I attended a very small middle school where most of the students were rich. There was one girl in particular who was dropped off every morning in her parents’ luxury cars and was the first to have the latest designer handbags (we were so jealous, lol). She would always scrunch her nose when other classmates brought lunches that weren’t pasta salads or sandwiches. She was always chosen first for sports games and made those chosen last feel terrible, and she would hand out invites to her exclusive birthday parties to just her friends in front of the entire class.
Anyway, in the area we lived, there’s an exclusive all-girls high school that was notorious for being very selective with their students. Naturally, she wanted to get in super badly. Probably because she thought she was smart enough but also because her parents expected her to. Four girls in our class (including me) took an extensive entrance exam, and it turned out that we all got in except her! She lost it. She sulked in class and cried when our teacher made an announcement to congratulate us. The next story will make you treat everyone around you with kindness.
Med School
A friend of mine from college whose parents were rich enough to have a multimillion-dollar home in America and in Europe used to crap on me for saying I was happy to go to whatever medical school I could get into. I ended up getting into my state school, and she responded by saying that she could get into that school in a second because her mom has connections in the admissions department. All through college, she had this attitude with me about how even though I was doing better than her in classes, I was going to go to whatever school would take me, and she was going to go to her dream school because that’s just how the world works.
I checked up on her on Facebook this year, and… she’s not exactly at her dream school. It turns out she is at her state medical school, which is actually significantly lower ranked than the one she was making fun of me for attending. I don’t want to say I was hoping she wouldn’t get in anywhere because that’s a little harsh, but I was happy to see her get put in her place a little bit. The girl in the next story was taught a valuable lesson at a young age.
The Brat
Me. My family’s financial situation was weird, so there was a time we were really doing extremely well. We had nannies and drivers, but at the same time, I was sheltered by my fam, so I had zero social cues and tact. I was a mix of a spoiled brat plus having no clue I was acting like one. I also was very rude and didn’t say thank you or please. Not because I didn’t want to, I was just stupidly lazy to say them. I have a cousin who is less privileged than me. She didn’t like how spoiled I was. We had a fight where I left her out on a playdate.
My stupid response was I’ll buy her chocolate milk. She snapped at me publicly about how I would never have friends if I think I could just buy people off. Those words stuck with me. In a cruel twist of fate, I went to a private school with classmates who are millionaires or trust fund babies, 20x richer than I am. Because I was less rich than them and fell into some financial hardships, I got bullied a lot for it. The next story is about not taking anything for granted.
The Downgrade
My friend in high school had two parents with pretty good jobs. She had a lot of name-brand clothes, bags, etc. She got a big solo trip abroad once a year. Her dad would buy the plane ticket, and her mom would upgrade her to business class. I once invited her to come on a family vacation with me to Disney World. Note that this is a huge deal because we live so far away it takes 20-plus hours and multiple airplanes to get there. She said, “No thanks, it’s really far away, and I can’t spend that long in economy class.” Last time I invited her anywhere.
She was all set to go to a really prestigious, expensive university in Switzerland, too, paid for by both her parents. Then her mom died. Her newly single-income household wasn’t poor by any means, but all the little luxuries just weren’t there anymore. She still gets her big trip abroad (barely), but it’s only ever economy class now. She didn’t get to a Swiss university because her dad couldn’t pay for it on his own. The guy in the next story just needs to stay off the roads if he knew what was good for him.
Stay In Your Lane
I recently had a kid I suspect was trying to commit insurance fraud call the police on me. There are “protected bike lanes” on the campus my partner lives on, and they are full-size lanes and are to be treated as regular motor vehicle lanes. He was traveling against traffic on a boosted board. He was supposed to stop at an intersection and yield to me as the first to arrive. I started my turn from a complete stop as he suddenly flew into the intersection, got all the way past my car without an issue, and then threw himself on the ground.
He jumped up and cussed me out, yelling about how I “busted his watch,” pulling some expensive watch out of his POCKET. To shorten the story, the police came and reprimanded him for being in the wrong lane and going out of turn, then apologized to me for wasting my time. The kid in the next story needs to be grounded for life.
Call Security
I had a snobby pre-teen come up to me once at a shopping center and tell me to give him my hoodie (a nice wool knit I got for Christmas). Obviously, I said no and started to walk off. Then he offered me money. Still, I said no, and he started getting aggressive. I told him to leave me alone. He comes back to me with his mom, who said she was calling security for “harassing her child.” I said sure, do it. He was really smug and told me I was screwed. It was kinda surreal to see someone like this IRL.
Security had the obvious response. I told the kiddo and his mom to leave me alone. Mom argued about how the “staff” shouldn’t act this way and how I should be fired for not directing her child to where to get my hoodie. The security guard told her to think hard about whether I worked there or not. She started poking him in the chest and demanding to speak to his superior. He had to lead them out of the mall. The next story proves that there’s nothing wrong with a good old-fashioned public humiliation by your parents to set you straight.
Public Shame
I had a kid in my senior class of high school who was an absolutely terrible person. His dad owned a construction company, and they had contracts with our city, so they did very well for themselves. He was always talking down to anyone he wanted, but also he got his butt kicked a few times because of it. Well, he never did schoolwork, was always getting kicked out of class for being a disturbance, etc.
His dad one day came to the school, walked into his classroom, and berated the crap out of him because the counselor told him that he had absolutely no way of graduating and needed to enroll in a secondary school. He took his car keys, his phone, and all the allowance he had given him minus money for the bus. He left school a couple of weeks later, and I believe he moved.