23 Stories From People Who Dated Into The One Percent

Hearts are in high places when love climbs the tax brackets.

Ever wondered what it’s like to date someone whose wallet is as thicker than a brick? Well, someone else did to and asked the question on Reddit: “what is it like having a relationship with a rich person?” The answers came rolling in, and let me tell you—it’s a whole different world. I’m not talking about your run-of-the-mill well-off folks. No, I’m talking private jets, islands as birthday gifts, and more zeros in their bank account than in a math test.

Drawing from the juicy tales of those who’ve mingled with millionaires, we’re peeling back the velvet curtain on the high life. Whether it’s the luxury or the quirks of having a significant other who can probably buy a small country, these stories from the moneyed-up dating trenches are as enlightening as they are entertaining.


#1 My wife comes from a wealthy family. Her parent’s net worth is low 9 figures. Their apartment and summer house are probably each worth $10m. 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 on 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 go to private school, and I don’t have to worry about their tuition. We take nice vacations (probably $50k paid for by my wife’s parents) once a year. We don’t spend our money on needless 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, travelled a ton, but 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 crazy with their money. They have nice things, travel when they want (sometimes flying private, sometimes not), and have a house keeper and property manager. They also have a 10 year old (nice) 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.


#2 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 is when they were getting intimate while she was on her period. She bled on his comforter that costs over 500 USD. 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 just replace it if it doesn’t wash out later. It was shocking to her that anyone could shell out that much to replace something on a whim.


#3 It’s like having an all-access pass to life’s VIP section, but sometimes you find out it’s overbooked with drama!


#4 I once dated a girl born 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 traveled for work, she started traveling with me and pretty much financed all the accommodations. I went from living out of 2-3 star hotels where I’d spend about $50 a night to 5 star outings where it was over a thousand bucks a night and I was always told to not worry about the money.

It was almost a year of us bouncing from one city to another, one high class hotel to another. We’d have fun, I’d handle work stuff, we’d make time to see some sights and do touristy s**t. Then her father found out, I guess, because he finally went back over his financials for the year (or maybe his business manager finally tipped him off to it) and he was definitely not happy. She had to go back home immediately, I was told that it’d be in my best interests to meet with him soon… so I took some time, flew out, and met with him.

He had a room that was meant to mimic a beach. Like, it had sand, and salty air, and some sort of elaborate wave pool, but it was indoors. It was weird but also kind of cool… we talked, he questioned if I was taking advantage of his daughter, which was fair given how over 6 months had gone by and she racked up tens of thousands of dollars in travel expenses. I explained the situation, and I was honest, that she insisted on traveling with me and paying for things. How she’d get upset if things didn’t go her way, and that while I liked her, she’s kind of controlling and bratty and I wasn’t sure what the future held for her… but I definitely liked her enough to find out.

He asked me if I liked her because of the money or if it’s because of who she is. I explained that I grew up fairly poor, I was always good at making my way and 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’m doing what I love and getting to make enough of a living to not have to work some 9-5. He laughed, and said that he liked me, and that if it worked out with her… he’d be more than okay with that. I thought I passed the s**t test.

We kept dating for a bit but let things cool off while she stuck around at home, since neither of us were all that sure of what he’d say or do next… then she got cut off, and she was *irate*, 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. Weirdly, it worked, but we didn’t talk much more after things ended. She did invite me to her wedding though, and I did go, and it was as awkward as you’d expect… but the food was awesome.


#5 If they’re really wealthy, you’d be surprised how superficial their relationships are with other wealthy people and just how normal that is. I thought Hollywood made that up for a trope but no. It’s all superficial but they have this weird almost familial obligation to maintain relationships with each other.

And also there are quite a few wealthy people who live somewhat meagerly but it’s not like some poor person cosplay they pat themselves on the back for. They’re either kinda stingy or they just don’t value materialistic things like that.


#6 I dated a guy who lives in a loft in East Village Manhattan, his dad is a relatively known artist. When I visited him at his place I had the impression that all New Yorkers live 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 NYC over the weekend too. But he didn’t allow me to be fully myself so that was the ultimate dealbreaker. He stil tried to reach out 7 years after we broke up but nah.


#7 One of my roommates in college dated a wealthy girl for a while and even as a bystander it was weird. I don’t know how rich you have to be to do this, but they self-insured their cars so they weren’t required to carry insurance. I remember she totaled her BMW and had a new Maserati in less than a week.

They would eat dinner at relatively fancy places most nights, and our fridge was constantly stuffed with their leftovers that I was eventually given permission to just eat, because 90% of the time it would just sit there for a week before getting tossed.

She supplied us with a basically unlimited amount of booze, weed, and coke for free.

But in many ways she was SHOCKINGLY sheltered and essentially lived in a different world. Not to say that she didn’t have struggles though – her family was held hostage when she was a kid because their captors wanted a ransom, and she definitely suffered from mental health issues that were verboten in her family so she covered it up with d***s.

She was also extremely kind though, and I hope that things are working out for her.


#8 It feels really f*****g good, 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/ me make up for it. 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 kids table to being forced to eat lunch in the bathroom.


#9 I dated a guy for a while who, while he wasn’t like 1% level of wealthy, his income was almost definitely in the top 10%. At the time, I was raising 4 boys on my own on what I earned bartending, so the income disparity was huge. He was a genuinely good guy. Kind, generous, absolutely willing to step up and be a father figure to my boys (3 of my own and I had custody of one of my cousins).

He took all of us on some amazing vacations. Bought all of us pretty much anything we wanted. I got a Mercedes convertible for my birthday (my *fun car, he also had already bought me a Dodge Durango for hauling all my kids and dogs around) He wanted to marry me and bought me a ROCK. When I moved out of the state we lived in, he helped me get a place, move, and for the first 6 months, paid all of my bills and gave me a “fun money” allowance of $5K per month. Told me, “you’ve worked so hard for this, take some time to just relax and enjoy life with your kids”

So what happened? Timing, mostly. And his insecurities. Both of us had just recently divorced. He had literally never really been single and was terrified of being alone. And my divorce and custody battle had been f*****g brutal – I was determined to just be on my own. The harder he clung to me, the harder I pulled away. I felt like he was buying me, and how could my kids respect me, how could I respect myself, if I stayed in a relationship based mostly on money. I felt like I was no different than a street walking prostitute — I just had a higher price tag. And that he didn’t love me, he would latch on to anyone to avoid being alone.

So I gave him back the Mercedes and the rock, went back to bartending, and we ended things. He was in a new relationship within about a week, and I raised my boys on my own.

I’ve told him – and 100% truly meant every word – that the best gift he gave me wasn’t the car or jewelry or the great trips. He gave me the gift of time with my kids. The divorce had been so nasty, we’d spent several years just going thru hell and trying to survive. And for those 6 months, for the first time ever, I had both plenty of time AND money to just enjoy life. And those 6 months were AMAZING. Every day was an adventure. My boys and I lived a life that most people can only dream of and I’ll be forever grateful to him for that.


#10 If you’re a poor person dating a rich person it’s kind of s****y. Makes you realize how disadvantaged you were your entire life lol.


#11 It was a chore, always wanting to do things I couldn’t afford and always offering to pay. Now, 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, like sure I can’t afford to treat us to the 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.

She would always jump ahead and pay, would always refund me the few times I managed to get in there first. At first I thought she was trying (misguidedly) to be nice but then 5 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 had told them. 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.


#12 About 20ish years ago I dated a girl for a few months and her family would probably have been worth well into nine figures. She was one of four, all kids very high achievers, all really well grounded, all had a million provided to them for their first home when they were ready to buy. Plus drove $50k+ cars from the time they were 21. Lived in a mansion in a great suburb, had holiday homes on tropical islands and ski fields etc

I went on a holiday with them – paid for my own flight – and couldn’t believe how well organised everything was. They owned the villa we stayed at, but when we all arrived the beds were made, all the blinds and windows had been opened, the pantry and fridges were fully stocked (she’d texted me a few days earlier confirming what my favourite beer was which now made sense!) and the pool was glistening. Chef came in on the first night to cook dinner, and then whilst 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 didn’t suffer fools, and nor did they waste any time doing things they didn’t want to do (outsourced LOTS!). Her father and grandfather had made their money providing precision manufacturing of parts for assembly lines – they had individual widgets that retailed for $100k+ 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 48hrs if something specific broke. It really introduced me to the idea that there are so many multi, multi millionaires out there with businesses that we barely even know exist because we just never encounter their products.


#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.


#14 I married into a hugely wealthy family. My father in law was President of an international medical staffing firm. He retired 3 times from the company and each time had a bigger retirement package.

My wife is cultured beyond belief, fluent in at least 4 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 the wealth actually practices 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 4 seasons a manager came over and called my F-I-L by name and pushed us to the front of the line. We were treated like royalty that week.

Or for my wedding to his daughter. Not only did he foot the bill for everything (Wedding reception consumed 12.5 gallons of Patron) he flew my wife and I 3 week honeymoon anywhere in the world on his dime.

He gave us his AMEX black and said have fun. 6 countries well over 100k in a honeymoon never said a word.


#15 Once had a short term relationship with someone who’s grandfather was a Canadian senator for like 15+ years. Whole family rich as f**k, old money, super WASP-ey, been in Canada for like 200 years and has always been rich and connected since they got here. My family has been in Canada 250-300+ years, lived in all the same places (like eerily so… same townships in southern Ontario, moved to a different province at same time, same / neighbouring communities stretching back 200 years), but mine has always been lower middle class. She hasn’t accomplished much aside from following her dad’s footsteps and training to be his occasional assistant. She isn’t rich, but knows she can always rely on bumming off dad / gramps and having s**t paid for her like being given dad’s used car, endless ski trips, Caribbean resorts, etc. She is very street smart, ambitious and a hard worker, but a complete narcissistic sociopath and liar who knew anytime she batted her large, pretty eyes and pretended to be super nice and bubbly, she would get pretty much anything she wanted. Nobody would believe me if I told them she’s a complete c**t (and a world class liar) who is only using them for her own selfish purposes. I feel sorry for anyone who thinks she’s their friend or whoever she’s living with now- they’ll only find out too late who she really is, if they’re lucky.


#16 I dated a very very rich owner of a national aerospace/heavy mining factory who 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…


#17 I dated a guy who was living off a trust fund. We got along great on a personal level but there was just such a gap in life experience. Like his family owned oceanfront property that was basically a mansion and summered there. He didn’t understand that for normal people like me, just going to the beach at all was a special thing. He didn’t understand why I couldn’t just buy whatever I wanted if I want it. That if I want something like a video game console I had to save and budget for it. That it was a really big decision. His “job” was basically just a hobby he did a few hours a week when he felt like it so he had no concept of having to actually work for what you have.He would get a car, have it like a month then want and get a new one. But what became the biggest issue was the dynamic between what we could do for each other, which got really uncomfortable. He’d shower me with gifts and take me fancy places, and at first it was awesome, like being a VIP. But it quickly got overwhelming. And I felt really bad because I KNEW he was doing it out of love and didn’t understand why it was making me so uncomfortable.


#18 I’ve been with my partner for 7 years . She’s a multi millionaire and we have a great relationship. I’m absolutely broke but I do work hard. There is a massive disparity in our finances but we just love each other. She’s beautiful, Sex is great. She can be a little bit precious sometimes, she expects certain standards. She’s posh, I’m not. I’m a good cook, she isn’t. we have experienced amazing trips, we have a Good life. I pay for our social life and she gets the holidays.


#19 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.


#20 My ex has very wealthy parents from Moscow. Not oligarchs, but also apparently not too far away from being it. Since I come from a relatively poor household (single mum without college degree), it was very weird to me in the beginning. She was super down to earth and one of the kindest people ever and didn’t buy these high end designer brands even though her mum asked her why she doesn’t treat herself with Louis Vuitton bags and stuff like that. She really changed my view on how to perceive money. When I grew up my mum always talked about money. For her it was everything for my then gf it was nothing. If you’ve none of it, money becomes the most important thing in your life. If you’ve all of it, it’s just something you use to get things you want.

Still, it was such a different world. When I booked a flight I’d do it months in advance to save money. She could do it two days before her departure. Missed a flight? No problem, book the next best one. Need money? Here, have 10k. I visited them once and they had an extra fridge just for champagne. Caviar at 1k a kilo. They went to the Maldives once, and I expected them to, of course, book a five-star hotel. Nope, they booked half of an island with a mansion and a butler. She could get any education she wanted. Private language teacher and whatnot.

I was jealous at the beginning but money doesn’t make you happy. She was very privileged but still had her problems. All the money in the world cannot heal you from mental health issues. Everybody has problems. Either you have poor people problems or rich people problems. Being poor just doesn’t let you compensate with something that costs money.


#21 I dated a girl with a very rich family right after college. It got kinda weird pretty quick. They liked and approved of me, and immediately started like making plans for me. The mother offered me $5K to quit smoking cigarettes because she “wanted boys, and smoking kills your male sperm count”.

I also had a lot of resentment come up (bc I grew up like stupid 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 damn near gave me PTSD.


#22 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.


#23 I have this roommate from high school who was raised up in a pretty wealthy family, and on his visit to me he asked me to company him for days in his luxurious suite and sharing the cost. I told him I was still a student, living a tight budget, and didn’t have that much money to spend on this. He was indeed surprised and couldn’t understand why someone didn’t even have the money to “stay in a hotel”. He probably had been working hard to understand what’s happening in the lives of the poor, but at that moment I literally felt that our friendship was more like that of a nobleman and his not essential, accompanying servant.