Wild Wealthy Dating Stories Go Viral, Prove Some People Are Crazy

Is it a smart idea to date wealthy people?

The answer, on the surface, certainly seems to be a very easy yes. Why not? Having money makes life easier.

That’s just a fact, and in theory, you’d assume dating someone with money would result in some positive outcomes.

However, some people would convince you to rethink that line of logic.

Wealthy dating stories go viral.

Now, I don’t have many deep thoughts on the subject. I will save my experiences for after we dive into what I discovered while scrolling Reddit Tuesday morning:

A viral thread breaking down a variety of different stories about poor people who dated rich people.

Yes, it was an immediate click, and it didn’t disappoint. Check out some of the stories below, and let me know your thoughts at David.Hookstead@outkick.com:

• She had a net worth of 40 million or so, and didn’t earn it due to her family being very wealthy. She was so disconnected with the real world, and was a true narcissist. Everything had to be her way, including aspects of my personality. It was constant nagging about aspects of me she didn’t like and wanted me to change. She was very manipulative and the moment I started to push back she ended it. Wild ride.
• I dated a girl, she was a nurse, and her dad was an HP CTO. She never had any problems with money, because new car, dad, new TV or washing machine, dad. She didn’t understand being a nurse usually wouldn’t grant her all that. Vacations in Aspen or Switzerland and whatnot. When I told her I most certainly can’t give her that life, she dumped me.
• She just seemed like she was very used to getting her way
• He invited me to things casually like you’d invite people for a cup of coffee, things that would take lots of planning and saving on my part. Like “Hey, I have to go to Vienna for work, wanna come?” And his hobbies were things like flying his own plane, and mine were free, like running and reading.
• He couldn’t grasp the concept that I have to work to live. When he offers to just take me next week to travel the world with him, he can’t understand I can’t just up and go. I need a heads up to request time off. I don’t have that sort of privilege because I have bills and rent to pay for lol and trust fund baby does not so.
• I grew up very blue collar poor. The men I knew fixed cars, re-roofed their own houses, knew plumbing and electrical stuff etc. My husband grew up very wealthy. His family had a massive house, a pool, a vacation home in Spain and maids. Honestly, the contrast was stark. The first thing he did after we moved in together was put liquid dish soap in the dishwasher. He didn’t know anything. He didn’t know the vacuum needed to be emptied. It could have been a deal breaker but he fully embraced his ignorance and learned. It was a whole new world and he loved it. One of my favorite memories is of putting up our first Christmas tree. He’d never been part of that and got so much joy from it.
• I hear you. We got invited to spend a weekend at a mountain vacation home of some wealthy friends. The wealthy husband and I went out to get wood for the fireplace. There were rounds cut but they weren’t split. He admitted to me that he didn’t know how to split wood. I showed him how to grab the splitting mall with gusto, put his entire body into swinging it all the way around, and hit the round with a “ring the bell at the fair” force that sent the halves of the round flying to either side in fear! His ear-to-ear grin as he split wood was priceless!
• Never knew. She worked a normal job, lived in a normal apartment, it wasn’t until someone told me after we broke up (she moved for work) that I found out her family was minted
• That in majority of the cases all is fine until you met the family and friends. You sit there like an idiot unable to relate to anything what they say and once you think some familiar topic appears, it ends up with a discussion about 10k baby strollers, wines or childhood memories about skiing in Switzerland or taking a trip to a seaside with their first Porsche. Their friends interests were mostly things outside my tax brackets, could’t even relate to typical girly discussions about makeup and clothing because their talks were about picking Birkin over Chanel, not about cute Zara top. Problems starts also when comes to buying a gift because there is no way you can match the amount of what they wanna buy you and any kind of decision involving finances when you want to go 50/50, but the holiday which your partner picked are your 5 salaries. Lot of people make it work, I tried two times and each time I felt out of place very quickly.
• Dated the daughter of a wealthy member of parliament for my country’s conservative party. During diner discussions at their home, it really hammered it home how little her mother (the MP) understood about the daily reality of being poor.
• The Family was an entity in itself and had rules. Relationships are EVERYTHING. The Family itself is a thing – the club, the parties, the vacations, the homes, the cars, the business, it’s all about The Family. The patriarch, the traditions. The schools. The business partners and the neighborhood and the club. It’s not a bad thing, it’s just different. I was raised to be independent and get the f*ck out of my parents house. They stick together like GLUE. everyone has a role to play, but they have security and they belong. I never belonged anywhere. I was raised by people who had kids because that’s what you were supposed to do, and then I got the f–k out of their house when I turned 18 and that was that.
• Partner born to wealthy family – generational subdued wealth. International trips a few times a year, live in housekeeper, best schools, NOLS, sports and art exposure. Good person, gave back with volunteering and donations. Contrast – could not relate to debt, fears of homelessness, or money anxiety. Biggest contrast: never afraid to try new things or make “mistake”. Took a job that didn’t work out, that’s ok – family will keep you afloat until you find something else. Broke a leg overseas because you took a skiing risk in Italy, no worries – we’ll charter something or find a way to get you out. I don’t have that kind of freedom.
• She was on leave from a work injury and she was saying she’s getting a certain amount. Her mom was like wow that not a lot at all. I was in the backseat thinking “she still makes more than me” She’s cool though, not spoiled by life or anything.
• My fiancée a while back was worried because her bank account balance was a little lower than she was comfortable with. Her “buffer” was more money than I had ever had in my bank account at any point ever.
• She was a full time professional fine artist (oil painter). Dad was a pioneer in green energy; whole family is loaded as a result. She was able to focus on school, earn her MFA, travel the world on residencies, etc. She was wonderful, and goes to show you that when you have a well adjusted upbringing, support, and the money to provide resources, you can be who you were born to be. Absolutely could not relate to the socioeconomic struggles of the people she dated though.

Now, it should go without saying that I’m not some wealthy aristocrat traveling the world. Not even a little bit. I’m a regular working-class guy from rural Wisconsin. That’s why when I get a taste of the high life it’s such a treat.

No secret bags of money here……but I have met a person or two with money. Honestly, most are pretty solid. No complaints here at all.

I’ve also met some rich women, and believe it or not, have dated a couple of women who come from money. I know, that’s probably shocking and undercuts my blue-collar reputation.

Here’s what I’ll say without diving into deep details: I know one woman who came from money who was so detached from reality and spending habits that it was mind-boggling. There’s being bad with money, and then there’s whatever this person was with a credit card in her hand. Just the dumbest purchases you’ve ever seen. Completely unnecessary accessories, clothes and gadgets? Don’t even think about it. Just buy it. Expensive dinners that aren’t even good? Sure, why not? I thought I was being pranked.

Nice enough person, but her financial skills would bankrupt anyone without resources. I’m just grateful my dad never witnessed that because he would have been beyond embarrassed.

Fortunately, that was a one-off. The other woman I dated who had money wasn’t like that at all, and my current fiancée is rather savvy with money – which is a very attractive quality.

Do you have any experiences dating wealthy people? I want to hear about it at David.Hookstead@outkick.com.