Dating the Super Rich: Fun, Fancy, and Occasionally Ridiculous

It’s champagne problems and jet-set drama when your date can buy a small island but forgets your birthday—welcome to the hilarious, surreal world of luxury romance.

“That good parents are better than rich parents.”

“Idea that having the money = having the controls, and being shocked when you’re just not impressed,.”

“Married a rich person. Regular problems arise but also unbelievably silly problems that only happen when you have too much money and no real problems so you gotta make some up. Extended family is building a 2 million dollar custom home in a rural area and are deeply distraught that the specialty plumbing expert they need to fly in from Norway in will cost $$$ to get a *consult,* which does not include install nor the inevitable future maintenance. Dawg you do not need fancy European plumbing in rural Idaho trust me.”

“Generally they can’t cook well, but somehow have the best kitchen gear.”

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“Not dated but was best friends with. They will never truly be able to even begin to comprehend your struggles, and therefore they will constantly dismiss and minimize your problems, which will lead you to be extremely frustrated. Trying to explain to someone that you can’t afford takeout and need them to do their dishes right now so you can cook, while they are telling you to just order out and put it on a credit card, most of the time it’s not worth the friendship.”

“I learned that every family has similar issues, rich people can just solve them quicker. .”

“That they are often insulated from the experience of peasant life. I was working 12 hour shifts in an industrial kitchen trying to save up enough for my next semester of college. Her friend (whose house had a fully stocked kitchen that only ‘the staff’ ever used) heard that I was working to pay for school and therefore could not take time off to go on a vacation. She took a moment to think about my situation, looked concerned with her furrowed brow, and then finally asked “why don’t you just tell your parents? school is a good thing, of course they’ll want to pay for that.”.”

“Equestrianism is a ***thing***

Also, pretty much any labor you can imagine, there is a service pool you can hire for it.”

“Money insulates the family from accountability. The behavior I’d see out of them sometimes over the smallest things was shocking.”

“No matter how humble and rational one is, dating someone several tax brackets higher will test one’s ego and self worth.”

“That most are actually way more humble than your larping rich person. Theres a huge difference in how the woman with the Gucci belt, LV bag, and a negative balance will treat you vs. The man in head to toe TJ Maxx but has 2mil in his account.”

“That even when they struggled in the early days, most have them forgotten what it’s like to not have money. They lose touch with reality real quick. A couple thousand here and there is nothing, meanwhile we live paycheck to paycheck(ish) and they cant understand why.”

“They are so poor all they had was money.”

“I learned how to play golf.

Her dad always wanted to chat with me about my future, plans, business opportunities, college choices…. Etc.

And he always wanted to discuss these over a round of golf at the country club. 

I really hate golf. 

Also, apparently $100k means nothing? Dude literally offered to buy me a new Mercedes, and have my old beater truck “disposed of”.”

“I find wealthy men make the best lovers.

Is that true?

No, but if you tell them that sometimes they give you their credit card and let you loose in the mall for an hour.”

“Money can’t buy good mental health.”

“An idiot with lots of money is still an idiot.”

“I grew up in what I can only describe as the identical median income household and had a decent job, so not poor, but I dated a woman who I met while she was in Law School who’s family was very rich. The subconscious expectations were overwhelming. I would plan a little surprise and she would expect something like a trip to Europe… She wasn’t trying to make me feel bad, her expectations were just so high from the world she grew up in.”

“You can have all the money and the world and still have bad tastes. He would offer me his card to go get stuff to make his 4,800 sq house feel like someone actually lived there. Otherwise it just had sparse ugly furniture and posters scattered around.”

“They simply can’t wrap their head around not having enough of everything at all times.”

“My college girlfriend of five years dropped me like a hot potato when her IBM vice president father passed away and left her a huge amount of company stock and in addition valuable real estate. My girlfriend found out that she was an heiress when somebody in the middle the night dropped off the will of her late mother that left most of the family assets to her. 

 My girlfriend had nothing to do with her family because her father was an absolute bully, but the minute she got her hands on significant dough suddenly I was not good enough for her. The class separation, in particular when the woman is from a well-off family is an absolute brutal fact. 40 years later this experience still hurts.”

“Class consciousness.”

“Money doesn’t make good parents, and bad parents plus unlimited resources just makes bad people.”

“They expect you to live like their lifestyle even though you can’t afford it.”

“I wouldn’t say I was poor by the time. Did, but I grew up very poor.

They were rich enough that they just didn’t even really think about paying student loans.

2 key things I learnt were:

1. They thought simply having money meant you were good with it

2. They had no concept of risk, sunk costs, or whether something was sensible as a stance (on anything, really). It was very clear it was all just about what they would like to do/have happen/believe is right in a perfect world. Not what is the better option in our circumstances, how real world restraints actually impacted it.

And to be clear, I don’t just mean financially.”

“My ex-girlfriend’s family was a stratosphere higher than my upbringing financially.

1. Constantly compared to members of their family and never can “match up” to their expectations

2. Huge difference in norms and what is acceptable or how things are handled ex. A summer bbq is a polo and slacks/fancy dress shorts event, not t-shirt and shorts

3. They keep personal events within the house to a creepy extent. “We don’t talk about the family outside the house” I was specifically told. Whereas growing up poor, everyone knows your business.”

“A lot of people want to pretend to be their friend and take advantage of them! Like, A LOT! They assumed I was doing the same and would talk openly about it to me… it was honestly disgusting!”

“They’ll still burn through your money first.”

“Being rich doesn’t mean someone’s happy.”

“That rich people are not evil. So many wealthy folks are incredibly giving, considerate and kind. I was raised in a household that preached those with money are selfish, self centered, and evil.”

“They will initially enjoy being themselves with you, as in themselves before they were rich. They will dote on you and buy you stuff (for whatever you are bringing to the relationship be it companionship or whatever).

And then, if it’s still going good, they will subtly try to change you, as they try to integrate you into their crowd, your clothing, your view on things (if they differ widely) and it will be up to you whether or not to do so.”

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