People Who've Known Or Dated Wealthy People Are Sharing The Most Shocking Things About Their Lifestyle, And I'm Fascinated

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29-03-2025

It's no secret that rich people have interesting lifestyles.
We often hear about what the tech CEO billionaires and nepo baby actors are up to, but if you've ever been curious about the lifestyles of non-famous wealthy people, you're in luck. In one Reddit thread, friends and lovers of rich people shared the wildest things they've realized about them, and it's veryyy interesting.
1. "I was married to a physician and had a good friend who was an opthamologist (multiple homes and investment properties, international travel fairly often). They would spend HOURS on the phone refuting a $20 charge."
– string1969
2. "Dated a girl who came from old money. Like hosting presidents at their Greenwich, CT mansion. All the grandchildren rebelled against it, wore old dirty clothes, shopped frugally, and did the dirty hippie thing. But she would begrudgingly go to Monaco every year and accept the yacht invites from the family."
"Also even if people looked unkempt, everyone in the family was very healthy. There was no struggle except for self imposed hardship, and that one cousin who got into drugs and was sent to a $50k per month rehab retreat in the Berkshires."
–one_pound_of_flesh
3. "I know someone who is a literal member of the aristocracy and lives in a castle but drives a beat-up old banger of a car. Same with clothes, etc. He will wear them until they have holes in them. You can tell by his speech that he's posh, but by the way he lives, you'd never know."
–mm_2840
4. "I know a guy who sold a startup to a larger company during the first dot-com boom. A total engineer nerd/inventor/technologist with buckets of money. I told him about my severe flight anxiety when making monthly work trips to NYC from the Bay Area, and he suggested that I take a G6 and avoid taking a G5 because the bigger windows help with that."
"I tried to explain why flying private wasn't really an option and that I fly commercial, and it was a bit of a 'it's a banana Michael, how much could it cost' conversation at that point."
–chiangku
5. "I dated a rich girl in college (1990s). The family was very wealthy from old money. She would be weirdly cheap about some things, like collecting money for the keg at a party, and the next week, would just write a check for an addition on her home (that she bought to live in while attending school)."
"Her dad had a barn full of mint vintage Porches. They had a debutante ball for her sister, which is still the fanciest, most pretentious event I've ever witnessed. I had to rent a tuxedo and decided to drop acid for it which was kind of terrifying but also awesome. So many sparkles."
–mattbnet
6. "It was shocking how out of touch she was with normal people. Her parents gave her three houses. One to live in and two to rent out. She couldn't wrap her head around why people don't always buy the best version of stuff."
–dances28
7. "My best friend from high school is super wealthy. She got her 19-year-old daughter a diamond bracelet for Christmas, and because it was an $800 bracelet and not the $3,000 one she wanted, she pitched a fit, threw the bracelet across the room, and had a meltdown. I just couldn't fathom being that entitled."
–frisbeemassage
8. "Ordinary-looking house, ordinary-looking car, ordinary-looking clothes. Not all multi-millionaires flaunt their wealth for everyone to see."
–Bizarre_Protuberance
9. "Nothing is not business. The new vacation home, for example, isn't just a plot of land he bought to put a house on. He bought acreage overlooking the ocean and subdivided it, with a nice double lot reserved for himself, so not only does he own the home, but he controls the covenant, HOA, and architectural board, and paid for the home and then some via the rest of the operation. The best part? The home is a business cost because it will be his son's 'office' and he's his 'employee.'"
–john_jacob_01
10. "My long-term partner's family lives in Southeast Asia. They are part of the royal family and are billionaires. I'm talking a $40 million house, an underground garage with 14+ luxury cars, and a school of employees working around the house. When we visited, one of the drivers picked us up in a Bentley."
"What shocked me most was how out of touch they were. We were traveling Southeast Asia at the time in our early 20s and just out of university, and they asked us, "So when you get back home from your travels, will you be purchasing a house?" We had just graduated and spent what money we had on travel. No, we would not be buying a fucking house.
The kids all had two cars, a weekday and a weekend car. It was amazingly flashy at first and easy to be impressed, but I noticed after coming away from it I always felt really depressed.
Obviously, they don't owe us anything, but they are literal billionaires, and we are back home with student loans trying to start our careers. All I'm saying is, if I had infinite money, I'd be helping out my entire family, haha."
–Maximum_Vegetable_80
12. "I have a friend whose family is well off. Not 'private jet' wealthy but wealthy enough that buying a farm because 'it would be fun' was pretty much all it took to pretty much buy Harvest Moon, and even a decade later, it isn't remotely close to 'breaking even' on just property taxes let alone the cost of it all."
"They don't consider saving money to be the same as lower stress. Something as benign as looking at two similar hotels. One is right at the conference center, the other is a two-minute walk away but is $50 cheaper per night (so $200 vs. $150 per night), which means that the convenience of not having the comically short walk is worth the $50."
–skaliton
13. "He wasn't wealthy, but his entire family was. What shocked me were their family game nights, where winning a board game could get you imported glassware, Michael Kors handbags, or top-shelf scotch."
–No_Brick_6579
14. "My best friend is a multi-millionaire due to his trust fund. He is just a normal dude who works 8-5 like the rest of us. The only reason you would know he's super rich is that he has a really big condo in downtown Chicago, which is like a $1.8 million dollar property."
"Other than that he occasionally picks up the bill without us noticing and never really flaunts his money. He's actually super embarrassed by the trust fund stuff because he feels bad he didn't earn it. If I asked him for $10k, he would probably give it to me, but I am the limiting factor there; I could never do that."
15. "Social relationships were much more calculated, chosen based on who they know or whether or not they make a talking point. And not just by her, but by people who wanted to know her. The conversation came up when she told me about her family's three houses in Oahu, and I reactively made a comment, 'Wow that's probably more than my family's whole net worth.' She did NOT like that."
–Automatic_Outcome_12
16. "For a few years, I had a boyfriend who was so rich that he misplaced a duffel bag with $300,000 in it, but I didn't even notice that he had misplaced it until months later."
–Embarassed_Rock_513
17. "Just calling and asking her parents for money whenever there was something she wanted was mind-blowing to me. She'd wanna order Uber Eats and just call her dad and go, "Hey, Dad, I wanna order some food for lunch. Can you Zelle me, like, 40 bucks?" And he would. This would happen multiple times a week with so much random shit. Her parents also helped her with all of her bills. Never seen anything like it."
–Cherrycokezerohead
18. "Went with him to Target for the first time. He was blown away at the variety of things they sold. Pots and pans in the same store with shoes? And toys? And pens? He always bought the highest quality of everything, so he's going to a pan dealer for pans. (Actually, he probably had his cook do this one), went to a cobbler for shoes and a pen store for pens."
–GlassCharacter179
19. "Not me, but a buddy was with a girl whose parents owned big lumber mills. We were at her place chilling in the indoor hot tub and watching a movie at her place when her dad and uncles got home from crab fishing on their yacht. They chartered a helicopter to take them there and back and at around 10 p.m. we were eating crab caught that day. We were 400 kilometers inland."
–UberBricky80