20+ Stories That Show Unexpected Side of Rich People’s Lives

Some people go to great lengths to appear wealthy. They flaunt non-existent wealth, show off “designer” clothes, and flood social media with pictures of their supposedly extravagant lifestyle. But how do genuinely rich people live? We did some digging and uncovered various stories — from greed and honesty to naivety, loneliness, and even moments of recklessness.

• When I was young, I worked as a waitress. A super wealthy guy wanted to date me, but I wasn’t having it, even after his $500 tips. One day, I came to work, and he was there with some important-looking guy. Then he announced that he bought the entire place I worked in. The second guy turned out to be a lawyer. We started dating. He took me on trips and bought me a car and a small apartment. But he was a very impatient person. He even paid people to follow me after we broke up. © Generous_Hustler / Reddit

• I have a very rich friend who always had a few girlfriends at the same time. He gave all these women expensive gifts, spent time with them one by one, and felt great. So he tells me a story.
  One of his girlfriends had a birthday. He gave her his credit card and said, “Buy whatever you want.” Now I quote, “This silly girl bought a book and a juicer and gave me the card back.” At that moment, he realized that she was the one. But she left him after she found out about his other girlfriends. © Overheard / Ideer

• I lived with a girl in college who was Crazy Rich Asian rich. She moved in for the company, otherwise her parents were just gonna buy her a house. She always wore this mini bag style purse when we were going out, and it just looked like a small plain black bag to me.
  I asked to borrow it for a concert one weekend because they had a super strict bag policy that none of my other bags met. She was like, “Oh sure, no problem.” I loved it and ended up looking it up to buy one for myself, and found out it was more than a year’s salary. And she let me take it to a music festival without a second thought. © chubbybunn89 / Reddit

• I used to date a girl a few years ago who had an “aunt and uncle” who were friends of the family. Over the summer, I was invited to stay a week in their house on the northern coast of Maine. The property was massive with a private beach and all but easily explained as it had been in the family for generations.
  I love cooking and was asked to prepare dinner for everyone on the third night of whatever I wanted to make, I was told to make a grocery list of whatever I wanted. Being on the coast and all, I wanted to make some whole cod with some family-style sides. I thought they were just being nice and going grocery shopping since I was not familiar at all with the area.
  The moment I knew these people weren’t just well off but wealthy was when the aunt placed a phone call and 3 hours later a seaplane landed at their dock with produce picked that day and then a boat pulled up with the cod I asked for. © PlentyLettuce / Reddit

• I know a lady who bought her kid a horse, then they bought the horse a horse for company. Then they decided they might as well build a stable. They now have about 8 horses and run an equestrian school. Imagine having the money to turn a child’s whim into a business. © TheLordofthething / Reddit

• My father is a very rich man. He started from scratch and came to a foreign country without a cent in his pockets. He’s never been involved in any dark stories, he spends all his free time with his family.
  And how much it pisses me off that people who have never bothered to get their butt off the sofa think that wealthy people are all thieves or criminals. Some have achieved everything through their efforts, work, and patience. Try to earn a penny yourself, envious people! © Overheard / Ideer

• I didn’t marry for love. My husband is a very rich man, we can afford everything. Years later, I’ve realized that this marriage was the right decision. I work in my favorite (though not profitable) business, I take care of myself, I buy expensive clothes, and we fly to luxury resorts. Our children do not need anything.
  And it’s clear to me that if I had to work myself and support the children, I wouldn’t be able to afford all this. Many people won’t understand me, but I am really happy. © Overheard / Ideer

• My husband’s best friend leads a reclusive lifestyle. He is very rich. He bought a huge plot of land on the outskirts of town, and there he built a two-story house, a mini-farm, and greenhouses. He breeds fish in a pond. He rarely goes out in public, he lives alone.
  He came to our wedding anniversary, and I don’t know why I told my friends about him. Then the guests watched as 4 women circled the man, who sat alone at a separate table. He put up with it for about an hour and then left. And my friends still ask me to introduce them to him. © Overheard / Ideer

• I once knew a very interesting man. He paid me a lot of money for just sleeping in the same bed with him. I had the keys to his apartment. I would come to his place, change into my pajamas, get into bed, and fall asleep. He would come over later and go to bed too.
  We had no relationship at all. But he introduced me to his friends, gave me advice, and told me about his childhood in poverty. A handsome guy, very rich and very lonely. © Overheard / Ideer

• I am writing this anonymously because I have only shared with 2 of my friends that my boyfriend’s net worth is over $250 million. There is no way to tell. When I met him, I was immediately attracted to his incredible sense of humor and intellect. He was dressed very modestly (I did not even notice his watch because it is not flashy; it is a $60,000 watch).
  We went on a few dates before I visited his home, which is not opulent by any stretch of the imagination. I even treated him to dinner a couple of times. He drives a SmartCar in Paris (where he lives most of the year). When he is in the States, he shops at Ross, and other discount stores, and always goes on the day that he gets a senior discount.
  He loves coupons, and when I show him ways to save extra money. He proudly wears a bracelet that I got him on sale for $160. On the other hand, he always flies either business or first class; owns over 100 properties in London, Paris, and Miami; has houses in those three cities, as well as in Cannes; owns a yacht.
  He is a decent, honest, and down-to-earth man who treats everyone with dignity and respect and gives much back to his community in terms of time and money. He brags about me because I have a career and I own my own home and greatly admires my intellect and thoughtfulness. © Anonymous / Quora

• When I lived in New York, I worked at a highly regarded hotel, the kind where you would see celebrities every other day. One time, a guest rented out a honeymoon suit just for their cat. © Unknown author / Reddit

• I unknowingly had dinner with a billionaire couple. Afterward, I was told about their wealth and I realized that their clothes were bespoke. Everything fit like a glove. Their nails were perfectly manicured. The wife was not wearing normal jewelry.
  They insisted on picking up the bill. They tipped $100 on a $180 receipt. They were both legitimately nice people, and I genuinely enjoyed talking/dining with them. © fossilnews / Reddit

• In my early twenties, I was a bartender at a super fancy yacht club. I was an incompetent employee and got the job entirely through knowing the right people. The millionaires always dressed super nice and humble-bragged about their success. The billionaires wore sandals and clothes from Target and Walmart and didn’t stand out at all.
  This one dude sat at my bar for 2 years with a 5 o’clock shadow and cheap t-shirts and just talked with me and the other bartenders about school and everyday life. Found out after 2 years, that he was the richest guy in there and had been giving the owner of the yacht club huge loans to keep it afloat. It still went under. © Nightmare_Tonic / Reddit

• I had a friend who taught guitar to the son of a very wealthy family. When my friend first visited their house, the parents led them into a huge room filled with many, many instruments, which the dad said was enough for a whole symphony orchestra. After the lesson, my friend asked why they had such a huge collection of instruments. The dad said that no one in the family played any instrument, but that he and his father had an interest in classical music so they found joy in just collecting the instruments. © Vincent_Gitarrist / Reddit

• I work alongside someone worth ~$750 million. They are 25 years my senior. He dresses smart casual as a base, then accordingly for more formal occasions. He notices all details of your attire including fit, watches, jewelry, etc. but would never comment on them. He talks to the public voice (kind, demure, pleasant). Then a talk to equals voice (blunt, aggressive, clear, incredibly fast-paced).
  He is rushed but not frantic as he controls everyone’s time around him. He allows almost zero people into his inner circle, but once you are in, he wants you to consume knowledge at the same rate as him. Constantly sending articles, studies, and reports at all hours of the night and wanting to discuss them in detail almost immediately thereafter.
  One thing I’ll also mention is he is action-oriented. When he has his “business hat on,” he is not asking for my informed opinion. He is asking for my direction. If I say anything, it has to mean that I stand behind it 100%. Period.
  I can be wrong, but I can’t be ambivalent in any detail, large or small. I vividly remember using the word “assume” and his reaction was the most fierce and real one I’ve ever experienced in business. Taught me a lot. © Shloops101 / Reddit

• There is a girl I know, a nice and sweet girl. Her father is a very rich man. He was divorced from her mother, but he supported both of them, gave them branded clothes, bought them a car, and paid for trips. But when the girl turned 18, he simply disappeared from their lives with the words “duty fulfilled.” © Overheard / Ideer

• My father is a very rich man with a pretty bad temper. A couple of years ago, he met a woman who, in just a few months, managed to turn him against his children and friends. We decided to stay out of it — he’ll play at love, and he’ll come round. It’s happened before.
  But recently we learned that he is rewriting all the property on her, so that the children didn’t get anything. And he genuinely doesn’t see what’s going on. He thinks it’s true love. And we are quietly amazed at how a person can be so naive at 60. © Overheard / Ideer

• Many years ago, I worked as a driver for a gentleman in Greenwich, CT. He was wealthy (millions) but one afternoon, on very short notice, he took me on a trip to Florida with the heiress of the Annenberg fortune (billions). We traveled with her and her entourage in her private jet from a private airfield.
  When staying at her residence, I remember meeting her and getting the feeling that she was deeply lonely. I’ve never sensed it as strongly as anyone else. She was quite nice to me. She spoke directly to me and paid attention to my answers.
  Something subtle I picked up on was how the people around her were very rehearsed — nothing natural ever happened. Ultimately, despite her extraordinary wealth, I felt quite sorry for her. © digentre / Reddit

• Rich people have a bespoke wardrobe that costs more than our cars. No logos anywhere on their clothes. © D***ieMcDookface / Reddit

• One of the signs of really rich people is amazing, unnoticeable plastic surgery. My cousin and I met a woman who looked like she was in her forties and discovered she was in her late sixties. Seriously, she looked amazing. She was the same age as my aunt, and we were floored when she happened to mention her age.
  My cousin and I compared notes afterward, considered some of the stories she briefly mentioned, and realized she was enormously wealthy. That’s when we realized that she had some very subtle plastic surgery. She wasn’t attempting to look like she was in her twenties, but rather aging very gracefully. © KayakerMel / Reddit

• I work in a niche industry that brings in a lot of wealthy folks. The wealthiest people I’ve helped are among the kindest customers I’ve ever had. One of them turned out to be the owner of the company that we get 1/2 of our product from. I didn’t know until I toured their facility a couple of years ago and was introduced to their CEO. She remembered me and commented on how knowledgeable I was with her products.
  It was a feel-good moment! I was seriously in awe, though. A woman CEO of a major international company still did her shopping! And not only did she listen to what I had to say, but she also took my advice too!
  She has an entire staff of people like me but liked my ideas enough to implement them. I would work for her in a heartbeat if she wasn’t 1.5 hours away. It was a good reminder for me to be kind to my customers. Sometimes in the busy season, I get a little cranky. © guinnypig / Reddit

Take a look at more fascinating stories about wealthy people that left those around them stunned.