16 Women Who Dated Rich Guys Share Their Stories — Good And Bad

There are all sorts of stereotypes about what it’s like to date a rich guy — some true, some not. Women on Reddit are sharing their personal experiences, and you might be surprised

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Some of the women confirmed a lot of peoples’ worst expectations: that the men were status-obsessed and held their wealth over their partner’s head. But others were pretty happy and found that their partners were grounded and unpretentious.

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1. Shopping As A Love Language

“It was f*cking awesome. We were married for a few years, and I’m still on great terms with his family. They bought my condo for me, and I have a modest closet of designer clothes that will last me years thanks to his sister and mom’s love language being ‘taking everyone shopping’ and their arrangement with everyone being ‘oh i’ll buy you this Alexander McQueen skirt, but to pay me back you have to…buy me coffee after.’ The man himself is an incredibly kind and thoughtful person. We’re still close, and I will probably be the godparent for his kids.” —


2. Not Like The Stereotypes

“My answer – I dated a wealthy guy (by his earnings, 7figs, not inheritance). He was incredibly sweet and kind and financially responsible. I was surprised at how he wasn’t conforming to the stereotypes, likely bc he grew up poor. He didn’t make me pay for anything, and was willing to pay for luxuries for both of us. I broke up because his schedule was stressful & all about being a type A person. He prioritised work over me, which I understand, but it made us incompatible. We’re still friends though.” —


3. Not Able To Contribute

“I dated someone who made about double what I did, although not necessarily ‘wealthy’ on a global scale, and let’s just say I could never forget about it. It was a constant feeling of not being able to contribute enough.” —

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4. Obsessed With Appearances

“I dated a really wealthy guy when I was younger. He was nice but obsessed with appearances, and so was everyone in his family’s social circle. I met the wife of one of their super wealthy friends and her first comment to me was ‘oh my gawwwwd you are so skinny! You’re gorgeous’ and it was just so f*cking weird.

We broke up because he was seeing someone else on the sly, and 6 months later she had his baby. He came begging me to get back with him a year later and of course I said no. The unfortunate part is both our mothers kept pushing us to get together and mine still hasn’t forgiven me for rejecting him.

Then when I was finishing university as a poor student I started dating someone wealthier than me. Low 6 figures income, but worked hard. We were so compatible, we had all the same hobbies (mountains, hiking, fishing, skiing) and a lot of the same goals. His family are farmers, he was so down to earth. We started dating exactly 17 years ago today. Now we are boring, kids and a house and pets, our incomes are a bit more similar and we are getting grey hair.” —


5. Terrible

“How wealthy are we talking? Wealthy in comparison to me, or wealthy like in a Forbes magazine? I can answer the former. Terrible. Dude would take me places I was uncomfortable going, and had no problem blowing money on frivolous things. He was also pretty stuck up, and VERY concerned with appearance. For example; going to the mall to walk around. Jeans and a tee were a little trashy, but Lululemon workout clothes were okay. And makeup was a must at pretty much all times. Dude could have just been an awful person, so I don’t specifically blame his money, but I will definitely think three or four times before dating someone who makes twice what I do again.” —


6. Great

“It was great. I married him, went back to school and now I am wealthy on my own and he is retired.” —

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7. Knows The Value Of Money

“So I’m currently dating someone who I consider wealthy, in comparison to me and in comparison to people his age. It doesn’t have any influence whatsover. He was raised to live modestly and know the value of money, so he doesn’t spend a lot of and he doesn’t make me feel uncomfortable by inviting me to fancy restaurants, paying everything for me etc.” —


8. Not Flashy

“My husband comes from old money, which means he isn’t flashy at all. The man drove a used 2006 Chevy Tahoe for 9 years before finally ‘splurging’ on a new Toyota Highlander hybrid. Fortunately this means he is very down to earth and he spends his money only on things that can be considered an investment (e.g. real estate). So I get a wonderful man with a large safety net who is not flashy, but who will never have a mortgage or any other loans. I pay a lot of bills because I have great income (especially with no housing expenses) and he appreciates me for that so much. It’s a wonderful balance and I live a very blessed life, but nothing crazy like designer clothes and Porsches. Just goes to show that it’s all about the person you marry, not whether or not they are rich.”


9. Felt Like I ‘Owed’ Him

“Honestly, it felt really weird…I’m not the type to feel comfortable with someone paying for everything, buying me things and I felt like I ‘owed’ him something so I ended it.” —

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10. Uncomfortable

“Terrible. I was lower class, 2009 recession, fresh college graduate and working part-time. By the 3rd date I had nothing to wear to dates anymore. He insisted on going to upscale expensive places and would meet with a lot of friends there. I really looked like the odd one out, even in my better dresses. I tried getting him to downgrade the places, so that I could dress more casual and not be stressed about the check, but he didn’t want to, he was accustomed to a certain environment. I have no idea why I accepted to date him in the first place. He was really nice, but I felt uncomfortable the whole time.” —


11. The Third Person

“When I did not want to proceed and gave him some very reasonable explanations about our low fitting, he said, speaking of himself in the third person: ‘But he is rich.’ Yeah well that was the final nail in the coffin.” —


12. Addictive But Not For Me

“Seriously, after dating a wealthy man for 6 months, I can understand how gold diggers are made. The life of luxury is addicting, but there honestly wasn’t a lot of substance to our relationship and I figured out his lifestyle and the world he lived and worked in wasn’t for me.” —

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13. Not Honest

“I dated an extremely wealthy guy. He was the ceo of multiple companies, one being worth over $400 million. He was very kind to me when we were together and offered to pay for literally everything (shopping trips to harrods included). The problem was that I was the 3rd person in what I assume is an open relationship. He got engaged to that girl the same week that we shared a bed. I don’t understand their dynamic but it’s not something I want to get involved in again…money or not. It’s not worth it. We traveled a lot and ate at all the best restaurants and stayed at best hotels (hotel du cap eden roc being one of them). I don’t regret the experience but I wish he was upfront about what was really going on. He mislead me to think we were exclusive. He told her the truth but he knew I wouldn’t be okay with it.” —


14. Power Imbalance

“It was awful. He came from family money and it made him feel like he had more decision making power in the relationship. (We didn’t live together and I had my own money). His parents also looked down on me and acted like I should be grateful they even gave me the time of day. I wish I could have seen their faces when they found out I had the nerve to break up with their precious darling boy. Never again. I have no idea what I even saw in him.” —


15. Obedience

“He paid for everything. Bought me expensive gifts that I didn’t want, ask for, or even like. Then he used these gifts to demand obedience because I owe him. This experience probably isn’t typical, but it is my experience.” —

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16. Nice and Normal

“He was incredibly nice and thoughtful, and just normal. He liked taking me to very posh restaurants. It was the wrong timing for us. The wealthiest people I know that are from old money are also just very normal. Nothing flashy when it comes to every day life, apart from a good private school for their kids. A few years ago they were going on a huge. long-haul trip as a family, and the travel agent asked her if she was sure they all wanted to fly business (they had 3 kids) because it was expensive. I kind of just laughed inside – they were rich enough to charter a plane if they wanted to, but humble enough to fly economy on short flights to teach their children what normal is. Grandparents were the same. They treated everyone the same, whether they were rich or poor, famous or unknown: with open arms and respect.” —


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