15 People Revealed Shocking Secrets About Dating The Rich, And You Should Brace Yourselves For All The Drama

“Regular” people didn’t hold anything back, and revealed what it’s truly like dating someone hellaaaaa wealthy (like…we’re talking big bucks, folks).

So, here are some intriguing stories of “normal” people dating the rich:

Note: Some submissions are from this Reddit thread.

Note: Some submissions include topics of domestic abuse. Please proceed with caution.

“I once dated a girl from a very rich family (like, ‘they own sports teams (plural)’ level of wealthy). She had zero concept of working to earn a living. She grew up pretty much having whatever she wanted, whenever she wanted it, and when we met, let’s just say she was very assertive and it was definitely working for me. When she realized that I had traveled for work, she started traveling with me and financed all the accommodations. I went from living out of three-star hotels where I’d spend about $50 a night to five-star outings where it was over a thousand bucks a night, and I was always told not to worry about the money.”

“It was almost a year of us bouncing from one city to another, one high-class hotel to another. Then her father found out because he had gone over his finances for the year (or maybe his business manager had finally tipped him off), and he was definitely not happy.

She had to go back home immediately. I was told that meeting with him would be in my best interest, so I flew out and met with him.

He had a room that was meant to mimic a beach — it had sand, salty air, and some sort of elaborate wave pool, but it was indoors. He asked me if I liked her because of the money or if it was because of who she was. I explained that I grew up fairly poor, and I was always good at finding ways to be happy with what I could manage. I was fine with the relatively cheap hotels and everything else I did before her because I was doing what I loved. He laughed and said that he liked me and that if it worked with her, he’d be okay with that. I thought I passed the ‘test.’

We kept dating for a bit but let things cool off while she stuck around at home since neither of us was all that sure of what he’d say or do next. Then she got cut off, and she was irate and blamed me for it because I said that I didn’t care about the money.

I tried to explain myself, but she wouldn’t listen, and we pretty much fought every time we spoke until she broke up with me to get back in her father’s good graces.”

—u/TheTrueGoldenboy

“I dated a girl with a very rich family right after college. It got kinda weird pretty quickly. They liked and approved of me and immediately started making plans for me. The mother offered me $5,000 to quit smoking cigarettes because she wanted ‘grandsons, and smoking kills your male sperm count.’ I also had a lot of resentment come up (because I grew up ‘poor’). They had different wings of a mansion and I grew up thinking people with a garage fridge were loaded. The amount of things they took for granted really got to me. The girl was great, but stepping into that world nearly gave me PTSD.”

—u/notMarkKnopfler

“Not me, but one of my friends is in an undefined sexual relationship with a rich guy. He offers to do a lot for her, but she’s hesitant to accept any of it. The biggest thing she described to me was when they were getting intimate while she was on her period. She bled on his comforter that cost over $500. She was extremely apologetic and wanted to try to clean it, but he insisted it was fine and that she relax. He said he could replace it if it doesn’t wash out later. It was shocking to her that anyone could shell out that much money to replace something on a whim.”

—u/souleaterevans626

“About 20 years ago I dated a girl for a few months and her family was worth well into nine figures. She was one of four (all kids were very high achievers and all really well grounded). They each had $1 million provided to them for their first home when they were ready to buy (plus they drove $50,000 cars from the time they were 21). They lived in a mansion in a great suburb, and had holiday homes on tropical islands and ski fields.”

“I went on a holiday with them and paid for my own flight. They owned the villa we stayed at, and when we all arrived the beds were made, all the blinds and windows had been opened, and the pantry and fridges were fully stocked.

The pool was glistening. The chef came in on the first night to cook dinner, and then, while we were eating, he cooked up a whole bunch of stuff that we could reheat/eat over the course of the long weekend if we couldn’t be bothered going out.

They were really, really lovely, but at the same time, they had expectations about things that would just never cross my mind. Despite being unfailingly polite, they couldn’t deal with ‘fools,’ nor did they waste any time doing things they didn’t want to do.

Her father and grandfather had made their money providing precision manufacturing of parts for assembly lines. They had individual widgets that retailed for $100,000 because they were literally one of two companies in the whole world that were trusted by a particular automotive business to get them back up and running within 48 hours if something specific broke.

It really introduced me to the idea that there are so many multi-millionaires out there with businesses that we barely even know exist because we just never encounter their products.”

—u/Aggravating_Bus_6169

“It felt like a chore, always wanting to do things I couldn’t afford and always offering to pay. I don’t mind a partner paying for me now and then, but I want to pay for the stuff I can afford when we do them. Sure, I can’t afford to treat us to a fancy meal, but when we stay in with a pizza, let it be on me. A trip to the cinema — it’s cool, I’ve got it. Let me do my part even if it can’t be as big as yours. I’m a partner, not a ‘charity case.’ She would always jump ahead and pay and would always refund me the few times I managed to get in there first. At first, I thought she was trying to be nice, but then five months into it, I found out her family/friends thought I worked in a bank (which I did, but as a cleaner and not whatever role she told them). It was all about appearances to her in the end, and I’m not one to hide who I am to impress others. So, that was the end of it for me.”

—u/Bean-Penis

“My wife comes from a wealthy family, and her parents’ net worth is low nine figures. Their apartment and summer house are probably each worth $10 million. I grew up middle class with both my parents being teachers. Honestly, I think I have a pretty perfect life, and it is because of the generosity of my wife’s parents. I work very hard and make a good salary, but at a nonprofit, because I don’t really need the money, and the work is meaningful to me. I have a multimillion-dollar home with no mortgage. My kids attend private school, and I don’t have to worry about their tuition. We take nice vacations (probably $50,000 paid for by my wife’s parents) once a year. We don’t spend our money on meaningless things, but we don’t have to ever worry about money.”

“My in-laws didn’t come from money — they actually grew up pretty ‘poor.’ I think that made a big difference in the way my wife was raised. She had everything she wanted and traveled a ton, but she wasn’t (too) spoiled.

Today, my in-laws’ main occupation is philanthropy — they give away millions of dollars a year. They have no financial worries but never do anything bad with their money. They have nice things, travel when they want (sometimes flying private, sometimes not), and have a housekeeper and property manager. They also have a nice 10-year-old car, don’t care about luxury items, and lead a very down-to-earth life.

I’ve been married to my wife for 20 years, and I’m just lucky.”

—u/TheDapperDragonfly

“I am currently dating someone rich, and it feels weird to me that she’s able to buy things without a second thought. She tells stories about how she traveled the world while I only remained within the US. She attended Beyoncé and Taylor Swift concerts and had front-row tickets for both. We could be talking about going to an event or planning a trip, and she’ll be ready to purchase/book everything right then and there. Whereas if it were me, I would need a couple of days to sleep on it.”

—u/My_Cock_Is_Throbbing

“I married into a wealthy family and moved overseas to live with them. They aren’t considered particularly wealthy in their country, but from my home standards, they certainly live in a mansion! I grew up with split parents: one below poverty and one middle-class who always worked. I saw life from both sides of the spectrum. It’s interesting to see how some people have kids (often adult kids) with no concept of money management. Buying designer clothes every week, eating out at expensive fancy restaurants, and ordering in every second night. Then they are surprised how at the end of the month they have no savings.”

“It’s so common to hear 30-year-olds getting casual handouts of cash from their wealthy parents. My family wouldn’t have been able to afford to do that on one side (albeit would go into debt to help you if it was an emergency).

Many of these families had a grandparent or parent that worked hard for the money, but the concept and ability to budget was never taught to the kids.”

—u/neelhtaky

“I dated a guy who lives in a loft in the East Village in Manhattan, and his dad is a relatively known artist. When I visited him at his place I had the impression that all New Yorkers lived in huge spaces like this (his bedroom alone was twice the size of my entire apartment). He was very doting and would splurge on me, and we would stay in nice Airbnbs across the city. But he didn’t allow me to be my full self, so that was the ultimate dealbreaker. He tried to reach out seven years after we broke up, but nah.”

—u/kurokamisawa

10.

“It feels really good [dating someone rich], but only when their wealth is balanced with self-awareness. They’ll have their out-of-touch moments, but their random acts of kindness towards strangers make up for it to me. Forewarning: when/if the relationship ends you will dread going back to your previous lifestyle more than the breakup. It’s like being exiled from the ‘cool kid’s’ table to being forced to eat lunch in the bathroom.”

—u/Delicious_Horror8928

11.

“I dated a very, very rich owner of a national aerospace/heavy mining factory. He drank, tried to have absolute control over me, and thought it was perfectly acceptable to drink himself unconscious in upscale hotel suites with me and wet the bad. Unfailingly. The third time this happened I ghosted him. For a few years, he’d contact me on his birthday…BIG NOPE on that one.”

—u/buckyfur1

12.

“I haven’t married into the family yet, but my long-term partner’s family is far richer than mine. They have a huge house worth over $1 million, two expensive cars, and holidays abroad every year. My family isn’t struggling too much anymore, but they’re significantly poorer. The difference in attitudes between my parents and my partner’s was quite shocking. His parents, though well off, are realllly tight with money, whereas my parents are generous to a fault and don’t care about having a lot of money. This became apparent when we both started university. My parents offered me £300 a month for food and living expenses (I paid my rent), which I declined because I knew it was a lot of money to them. My S.O.’s parents, however, begrudgingly agreed to give him £20 a week for food and living expenses. But, they consistently guilted him for this and acted like they had to work extra hours when this was clearly not the case.”

“They also made him work from an extremely young age — his dad signed him up for three paper routes at the age of 12, which paid almost nothing and took up large chunks of time outside of school.

And recently, they pressured him to get a job during the four-week break we have from university (even though he has seven exams to revise for). They did this so they don’t have to give him the £20 a week. This makes him pretty stressed and upset.”

—u/wtfisthatttt

13.

“I was shocked at how down-to-earth, caring, and giving very wealthy people are in real life. On the internet, they are vilified to the 10th degree, but I have never met anyone in that part of society who wasn’t charitable and generally nice to the people around them.”

—u/Foreverforaminute

14.

“He’s from an upper-middle-class family — they go on multiple vacations a year. They have a pool, boat, and a huge property with a beautiful house in a small, quiet neighborhood. My family was barely above the poverty line — my parents made sure I had what I needed, but we definitely went without often. The power and water would get shut off, and we never went on vacation. My S.O. and I met in high school during junior year, and have been together for nine years. The first shock was definitely the first Christmas we spent together. When we went to his house, I saw a mountain of toys (it easily came up to my waist). It was packed with things like Beyblades, Pokémon merchandise, and dinosaur toys. I thought to myself: ‘Wow, his brothers made out well this year.’ But nope — that was just one of the three piles of toys in the home. His was smaller, but full of more expensive toys — video games, an Xbox, and iTunes cards galore.”

“The most shocking part? He still had expensive presents at his dad’s and grandparents’ to open.”

—u/vanessag23

15.

And finally, “I married into a hugely wealthy family — my father-in-law was president of an international medical staffing firm. He retired three times from the company, and each time, he had a bigger retirement package. My wife is cultured beyond belief, fluent in at least four languages, and has seen the world that most of us could only dream of seeing in our lifetimes. My wife is also one of the hardest-working people I have ever met, and even with all of the wealth, she actually does charity to the point that I have to stop her. I never realized how influential the name was until visiting New York and staying at the Four Seasons Hotel. The manager came over and called my father-in-law by his name, and pushed us to the front of the line. We were treated like royalty that week.”

“This was the same deal when I married my wife. Not only did my father-in-law foot the bill for everything (the wedding reception consumed 12.5 gallons of Patron), but he gave my wife and I a three-week honeymoon anywhere in the world on his dime.

He gave us his AMEX Black card and said: ‘Have fun.’ We went to six countries, and the honeymoon cost well over $100,000 — he never said a word!”

—u/[deleted]

Note: Some submissions have been edited for length and/or clarity.