20 People Share Their Experiences Dating Those Richer Than Them

Published 2 years ago

We date to feel loved. We date to be accepted. We date to find someone who would be willing to accompany us for the rest of our lives. And love knows no bounds. It can power through any gender, through thick and thin, and through poverty and richness.

So it is sometimes possible for two people very far off in the economic spectrum to fall in love and date. One of them can be poor and date someone who is far richer than them. To know how that type of relationship would go, we consulted this Reddit thread. The community’s responses are very informative and enlightening enough to give us a feel for this kind of love!

More info: Reddit

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Image source: redbradbury, Chalo Garcia

If you have a lot of money, people give you so much free stuff all the time trying to earn your business or procure donations. Ironic that the people who can best afford to pay for the items get comped the most!


Image source: NewOldSmartDum, Andrea Piacquadio

I have been both really poor (chapter 7 bankrupt) and then pretty well off years later. I never thought of myself as rich until we replaced the roof on our house because it was time to. No insurance claim, no hail damage, just it was time. We had that “remember when we lost our home in a foreclosure sheriffs sale? Now we just replace a roof cause we should”.
What I’ve learned is that you make up new ways to stress about financial stuff but it’s all extra discretionary spending issues. New cars, new flooring, redone bathrooms, nice restaurants, kids colleges etc. Lifestyle issues, not life issues. The ability to just handle the necessities is such a massive relief to any family and should be really humbling to any of us fortunate enough to live that way.


Image source: RunningRunnerRun, bruce mars

How much easier it is to make money when you already have money.


Image source: ginger1rootz1, furkanfdemir

They live in a mindset that someone else will take care of it. My ex’s family had money. He did not. Told him that one month there was no money for food in my budget and he’d have to hand some over for it. He told me he had none and I’d have to fix the problem. Then he went on to describe for me in detail a toy he was saving money for. Asked him how much the toy would cost. He had $200 set aside to buy this toy that wasn’t going to launch for more than 3 months. But he wouldn’t touch it for food. I literally could not get it through to his head that there was no money for food, and no food NOW. It did not compute at all. Had him take me to local food banks. He did not come in. He went shopping while I was filling out paperwork for food. Came out of the food bank to find he’d dropped $80 on a book. “That money was from what I had set aside to buy new books.”


Image source: edwadokun, Cristina Anne Costello

Dated a girl for 3 years who came from old money.

She was fine but her family was beyond out of touch with the real world. They were nice people but incredibly removed from the rest of the world. They looked at me like I was zoo animal in the sense that they were so curious about my life/family. They’d ask me what it was like going to public school. How my parents immigrated. They were baffled that not everyone had vacation homes or traveled a lot.

The most interesting thing is that old money is much more powerful than new money. They belonged to these “clubs” that consists of other rich families and the influence they had was mind-blowing. Want to build a factory in an area not zoned for it? Within a week that was changed.


Image source: BlitheringEediot, Tim Samuel

Dated a man who didn’t work – lived off of a TrustFund. 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 go buy another $400 mixer. Nothing meant particularly ANYTHING to him.


Image source: problematicsquirrel, CafeCredit.com

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 of itself. Also he had no concept of how much anything cost. Was going to get some groceries for dinner and he gave me $300 to pick up some basics.


Image source: Newdiotnot, Nad Hemnan

Mine’s a bit on the positive side I guess.
I grew up dirt poor and I guess got to a point where I couldn’t dream big. My family is still poor.

I dated a guy who not only was a trust fund baby but he 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.

He’d organise spontaneous holidays overseas and fun weekend activities that cost money. Told me to leave my card at home. Then in the short time we dated, he coached me into 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.

Now I have money and can take my parents and siblings on holiday as well as put my siblings through university and help them out.


Image source: MakeRobAPirate, Paul Szewczyk

My ex was having problems with roommates at university. Her parents bought a $300000 condo for her to stay at while she finished her degree (2 years). They sold it for a profit immediately after. I can’t imagine not only being able to solve my problems with money, let alone make more off of them. She also assumed her family was lower middle class because she didn’t live in a mansion like her friends. She was very humble and was smart with her money, but it was very clear she could just call her parents if something didn’t work out. Meanwhile my parents were struggling to pay rent, meaning I was their fallback. Not the other way around


Image source: capricious_achelois, Davey Gravy

I learned just how productive having money can be. Something needs 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/ saved for?


Image source: Possible-Magazine917, Towfiqu barbhuiya

Just made me realise how expensive being poor is. They never have debt, never need to look at their balance too see if they can buy food, never pay interest on overdue bills etc.


Image source: Blundell1992, Niklas Bischop

That we’re hardly even playing the same game, nevermind by the same rules.

I dated a girl from old money, generational inherited wealth. Grandpa’s money, some corporate bigwig banker or something to that effect. 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 real 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 is 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. I wasn’t exactly poor growing up, but for the most part if it wasn’t strictly necessary for survival I didn’t have it. It was really eye opening how everything was taken for granted. Those specific people would be helpless in the real world if they lost all their dough.


Coming from the opposite side: I’m “rich” and I dated a poor guy and I felt very humbled. At first, I couldn’t understand why he couldn’t just go on vacation with me on a whim. I couldn’t understand that the reason why I would always have to drive the 4 hours there and 4 hours back to see him was because he couldn’t afford that much gas. I couldn’t understand why grocery shopping with him was sometimes at the dollar store while I shopped at Whole Foods. I couldn’t understand not being able to just ask your parents for money. He once told me that I was a product of my environment and it was very eye opening. Terrible relationship but I learned a lot about myself and the world

Source: eggheadslut


Image source: MerylSquirrel, Jorik Kleen

I only went on one date with him. He booked out the entire bowling alley so we’d have privacy for our date. It just seemed so shockingly wasteful to me, and it was bizarre to have a 20-lane bowling alley just to the two of us plus a fair sized staff who were left with nothing to do but look after us. I learned I’m very uncomfortable with that level of casual assumption that the world will rearrange itself to suit my whims.

Also he had absolutely no respect for personal space. I don’t think he was used to women not liking to be touched by folks they barely knew.


Image source: Good_nuff, Mike Renlund

I dated two dudes with trust funds.

I learned no amount of money can make you forget your mommy/daddy issues.


Image source: PhiloPhocion, fauxels

How real the ‘network’ or ‘bubble’ of it is.

It’s like the other side from the ‘it’s expensive being poor’ concept. It’s this weird internal community of people with money, and thus power, who are willing to make things happen as long as you’re ‘in’. I mean, I would meet people at a fundraiser or something and five minutes later, they’re happy to make a call that will get me a job at some huge firm. Or like, my then-boyfriend would say let’s go this concert. Tickets are $180 but it’s okay but a friend’s parents have a box, so we’ll just join them. Or even one time the dishwasher in our flat broke – but we didn’t have to pay a dime for repairs, because his friend from high school’s parents own the building, so they’re fixing it for free as a favour.


Image source: ch1kita, Danny Giebe

You’ll miss the lake house more than them.


Image source: chumabuma, Bingnan Li

My wife’s family has no concept of what a workday is.


Image source: Friendly-Sea1979, Nadin Sh

Grew up poor (now middle class) and at 18 dated a superrich guy. First thing I noticed was the food. Not just quantities but I also discovered so much food (like oyster, fresh fish, olives,..) things my parents could never buy.

I also had to learn etiquette. My parents brought me up well, I read books all the time, was a decent student and well-behaved kid.. but the way his family interacted was SO different. I had to learn a lot of unwritten rules that I wasn’t aware of.

I think in the end what I actually learned was that even though my childhood was rough (the amount of stress of not having enough money has probably impacted me for life), I valued my parents so much more. Once I had seen what life was like for rich people, I was just so proud of my family for making it work with so much less.


Rich doesn’t cure alcoholism

Source: questfor17

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Dating, poor people, rich, rich people, rich vs poor, richness
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