Wealthy woman on private plane

The High Life: 21 Tips on Dating Someone from the Upper Class 

Dating someone from a higher socioeconomic family can provide a valuable learning experience, particularly for individuals who come from different social backgrounds. It offers insights into a culture and society that may be unfamiliar and can sometimes be surprising. These interactions not only expose us to a different way of life but also open our eyes to potential opportunities and possibilities that we may have never imagined.

Cutting Back

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One user said, “They don’t know how to cut back because they only know the good life. No, sweetheart, we don’t need 3 vacations a year when you are unemployed.”

Concept Of Work

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A second user shared, “I lived with a horrendously rich friend. One thing I’ve noticed about him is that he’s completely incapable of grasping that if I stop working, I just stop being able to eat. He was confused about why I was worried about taking a week off work and didn’t understand I was worried I’d lose money.”

The Whole Place

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A third user commented, “I only went on one date with him. He booked out the entire bowling alley so we’d have privacy for our date. It seemed so shockingly wasteful to me. I learned I’m very uncomfortable with that level of casual assumption that the world will rearrange itself to suit my whims.”

Trust Fund Baby

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A reader commented, “Dated a man who didn’t work – lived off of a trust fund. Oddly, since he could afford nearly anything  – nothing had any value. He’d buy a $400 KitchenAid mixer – and burn it up making Christmas candy the first week. If he decided to make more candy – he’d just buy another $400 mixer. Nothing meant ANYTHING, particularly to him.”

How Much?

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This poster commented, “On a Friday night whim, my girlfriend decided she wanted some pie. I suggested we go down to the store. She rang her favorite restaurant and had a chef bake her her favorite pie. The cost was $170. A pie. Yes, she could afford to do it, but the problem was the complete lack of value. Nothing really mattered to her because she had that kind of money.”

Utterly Shocked

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A user added, “My dad started his own firm, but for the last 30 years, he’s been the owner, not the boss, and in the last 20, it’s done well enough that he’s now minor-league wealthy rather than well-off. My sister has never worked, and my mom was a stay-at-home mom. They will constantly plan family vacations for all of us and be utterly shocked when my wife and I can’t just take three weeks off to go to Australia with them.”


_A group of friends looking happy
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One poster shared, “I went to pick up a friend at her rich friend’s home many years ago. It was Tuesday 11 am. I was self-employed but got antsy when not in front of my computer (pre-smartphone). There were 4 rich friends in their 20s, sitting on 4 couches facing one another in their summer house across from Golden Gate Park; no conversation, music, nothing. They just sat there looking beautiful. I got jittery simply for being hard-wired to be working on Tuesday morning. The freedom they had stuck with me. I was a bit envious, a bit intimidated, very confused.”

Elite Social Club

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This user said, “I worked for several well-off families for a year or two, and this was my biggest takeaway. They were all cordial. For the most part, they all had a team of people that worked for them regularly on discrete tasks or certain aspects of their lives, and they ALL knew each other.  It felt like an elite social club that looked out for each other.”

Add An Elevator

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A poster divulged, “My ex built a new loft above her business, and originally it was supposed to have an elevator from her master bedroom to an office. It wasn’t installed at first because of cost issues. Well, she blew out her knee, and it was very difficult to go up and down the stairs. Her friends called her and said, “We called the guy who will install the elevator tomorrow. Just pay us back whenever.”  It was 25k, which included 7k rush order.”

Productive Finances

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A user commented, “I learned just how productive having money can be. Does something need to be fixed/ replaced? We can afford to. Want to do something fun or adventurous? Sure, let’s do it now. Want to eat healthier? We can afford all the ingredients. Like, what do you mean your life isn’t slowed down by a million different things that need fixing/ upgrading/ replacing/saving for?”

A Quick Helicopter Ride

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This user recalled, “I had a girl that wanted to take me to her parent’s vacation home for the weekend. But it was farther than my two-hour on-call leash as a firefighter. She was like no worries if you get called out on a fire. I’ll have my dad pick you up in the helicopter.”

Frivolous Spending

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One user added, “Our appliances would always die. We never owned a house, just rented, and for some reason, back then, you had to bring your own washer/dryer. Seeing my mother, with 4 kids, stress over the dryer dying again and how she would swing the laundry mat was something I’ll never forget as a kid. I married a guy from a well-off family and was blown away when he wanted to replace our dish towels because they looked ratty. Like, WTF dude? We use these until they disappear. We don’t just “replace” perfectly good dish towels. New dish towels were ridiculously frivolous to me.”

Kiss The Ring

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A top-liked comment said, “My ex-wife had a grandfather that was a multi-millionaire. Christmas time at their house was like being in another world. All the different family members would try to get a moment with the King and kiss up as much as possible. I spent my time on the ground playing with my kids and was happy to get out of there. About a week or two after the second Christmas, I got a phone call from Grandpa. He wanted to know what he could do for my family. I told him I didn’t want any of his money, but I would like my kids to know their great-grandfather. Later that year, he showed up at our place unexpectedly and spent most of the afternoon telling stories with me about his youth. He set up a trust fund for each one of my kids to have their college paid for a little bit after that. He told me out of all of his in-laws, I was the only one that never asked him for anything but to be himself.”

Money Earning Money

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A reader added, “He didn’t have any concept of saving money. It was always just there because his money was always earning money. Having money was an income stream in itself. Also, he had no concept of how much anything cost. I would go get some groceries for dinner, and he gave me $300 to pick up some basics.”

Afford Not To

Being Poor: man standing with pockets out to show no money.
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This user mentioned, “I wasn’t that poor, and she wasn’t that rich, but it was enough of a difference that I was shocked at how often she just took planes. Like, she flew more in the summer than I had my whole life. That and apparently, they go to Hawaii for a week every year, which was fun the time I got to tag along, but it’s pretty wild to me that they can just do that. Even if I could afford it, I don’t have enough vacation time to do that every year.”

Old Money

Man holding his face looking shocked
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One poster stated, “I dated a girl from old money, generational inherited wealth. I don’t think her father ever worked a day in his life, and her mother clearly came from money as well. Outside of her, I found every one of her family members out of touch and completely unrelatable. I got really good at biting my tongue when my ex’s siblings would complain about not getting a new car for their birthday when last year’s model was sitting in the driveway. They had no concept of the value of money and never had to do anything for themselves to get what they wanted.”

Incompetent & Entitled

Arrogance: man standing with a crown pointing to himself with an arrogant face.
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A user added, “My ex’s father was rich. My ex himself was not rich, did not understand the value of money, and was a spoiled brat who got a great job at a great company full of awesome people and then proceeded to steal from them. He was the single most incompetent and entitled person I’ve ever known, but he firmly believed he was the smartest person in any room he entered.”

Miserable & Unhappy

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This user shared, “I dated a guy for four years that had a wildly wealthy father. Private jets, extremely expensive cars, giant homes, paid for his children’s veneers/plastic surgeries, employed them all, etc. They were the most miserable, unhappy people I’ve ever had the displeasure of being around. It completely changed my view of the very rich and the facade they put on. The money was nice, but I would absolutely never, ever willingly associate with any of them again. They were terrible people. Very unhappy.”

Learned Value

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A reader commented, “I grew up dirt poor. I dated a guy who not only was a trust fund baby but also had a job as chief engineer and was making over $250k a year from that job. He didn’t need the money. I was making $70k. In the short time we dated, he coached me on how to get a better-paying job. Helped me learn and understand my worth and the value of my education and experience. While dating him, I quit my $70k job and landed a $100k one, then broke into the $200k a few years later.”

Dinner At The Zoo

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This poster said, “Dated a wealthy girl back in high school. Took her to Chilis with my parents, and I’ll never forget her looking around like I took her to the zoo. Made me laugh inside.”

Every Green Light

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Finally, a user shared, “Spent the first 8 years of my adult life with a woman whose parents had money. She had no conception of how hard life could be if you couldn’t just sell stocks to buy a new car or have someone give you a couple thousand to put you up in a new place. She pocketed her paycheck every two weeks. When we broke up, she had $30k in her savings account, and I was broke. Growing up with money is like hitting every green light and not having to worry about traffic jams.”

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