Men Share Their Struggles Dating A Woman Much Wealthier Than Them

Relationships are hard. Finances are hard. Making things work with someone from a completely different lifestyle than your own is hard. Being in a relationship with someone who has a lot more money than you can be like a perfect storm of "oh no." When that perfect storm slams into the fragile isles of masculinity and societial expectations ... well ...

One Reddit user asked:

Men of reddit, what are the struggles of dating a very rich girl?

And yeah, things got interesting. Firstly, there are some happy endings in here, so it's not all tragic. Chin up. I wouldn't do that to you. Secondly, a shocking number of responses didn't really have much to do with money. For most people it seemed to come down to a lack of ability to connect and relate. Finally - societal expectations and the weight they put on people really, really suck. Oh, and shout out to the phrase "wealth whispers" - which is something we'll be thinking on for a long time. Here are some of the more popular stories about men who dated much wealthier women.

3 Hours

A friend of mine dated a very rich girl that grew up a few hours away from us, they bought a small modest house and had a baby. Her family didn't like him because he was a construction worker and didn't have the "class" they expected. They built them a new huge house next to theirs and pressured them to move to it but my friend had a job and life that he liked and she was a stay at home mom. Anyway after a few years it just caused so much tension that their relationship ended and she moved into the house herself and he is basically screwed because they said if he tries to do anything legal that they will bury him. Now he has to drive 3 hours just to see his daughter.

- escloflowne

Punched In The Gut

I live in the Bay area. My girlfriend isn't super wealthy, but wealthy enough to live in an expensive area. Expensive for me, at least.

I love her so much, but it's difficult sometimes because I never have money for anything. She's always willing to pay for me but every time she does it's like getting punched in the gut. Even small amounts like for public transit. She's always very understanding but that doesn't make it any less difficult.

- WaffenWaffel

No Horses


Admitting financial struggles. When my wife and I were dating in university, her family invited me up to their cottage during the break between Christmas and New Years to ski, skate and otherwise play in the snow. I wanted to go, but I didn't know how to ski, and had no outdoor clothing appropriate to be out n the snow (no ski jacket, pants or boots). I declined the invitation, but my then-girlfriend was really sad and asked why. I had to admit I didn't have the gear needed and I couldn't afford them. She then passed it on to her family and when I visited them on Xmas day, they led me to a a room with 3 types of everything new with tags laid out on a bed for me to choose from. It was a wonderful gesture, but I had mixed feelings - I appreciated the gear very much, but I felt like a charity case.

Also, managing expectations of my wife for travel and expectations with children's activities- she was used to jetting away whenever they felt like it and had her own horses growing up. That's just not an option for us. We do OK and we're happy, but horses are not financially viable.

- BroodingBryanAdams

Keeping Up

Keeping up with her. She wanted to go on European trips, expensive vacations, expensive restaurants, etc. She made very good money and I was limited in my funds and had to spread it out. I couldn't just fly to the Caribbean at the drop of a hat. So, in turn, she left me for a guy who could.

- Runlikehell67

Ruined By Pride

I guess I had a different type than everyone else. We worked together and you wouldn't know she was rich unless you really got to know her.

She worked as a diversion, something to do and meet new people. She never looked at the price of anything, had a $5,000 watch, dolce gabbana glasses she would break at least once a month cause she's clumsy.

Very humble, very sweet and probably the hardest worker there (we were managers). The issue was that there was absolutely nothing we could do together that was new to her. She had more money and free time, her bucket list was completed by 22. There was nothing new or fresh within my... I dunno the word, realm? Ability?
We got along great and I found out from a mutual friend she was excited to be with someone not using her or groveling cause she was 'fuck you' levels of rich.

It was my pride I think that ruined it, nothing she did. I had issues letting her pay for everything and I was unable to show her anything she hadn't seen, I stopped being fun because I couldn't wow or impress her and it got in my head, she was perfectly happy doing normal things, but it wasn't enough for me, I HAD to impress her.

We lost contact years ago, I hope she's doing well, she was fucking awesome and deserves to be happy

- Necro_lancer


My roommate was very wealthy and her boyfriend ended up living with us for 2 years and I remember they would have the saaaame fights all the time. He came from a very poor household, tough family life, in a not-so great area of the city, didn't graduate high school, etc. He was supporting himself working as a bartender. Compared to his childhood financial situation he viewed supporting himself with a steady job as being successful whereas she was always wanting him to do more, be bigger, etc.

They also fought a lot over birthday gifts, Christmas gifts, etc. She would buy him really expensive gifts that he needed, but couldn't afford to buy himself. He needed new winter boots and a coat so she would buy him really nice ones for Christmas. A good coat and boots with one or two other items can easily get close to $5-600. He could never get her a gift of such magnitude. She was somewhat understanding that he couldn't pay for something like that, but he used to tell me he always felt a lot of pressure to match her really expensive gifts with really creative ones. He said he would dread holidays, Valentines day and birthdays, because he would get so stressed out trying to constantly think of creative ways to match her really expensive gifts. It seemed to me like he was getting really bitter about having so much stress over creating a gift vs. her being able to spend 5 minutes using her parents money to get him something.

I think it was also tough because she wanted to do so much stuff and had the financial security to do it. She wanted to travel a lot and he just couldn't afford it. She would pay for him sometimes, but that bothered him. I met up with them once when I was living in Thailand and she kept using phrases like "This is so cheap for..." Like she would insist we got to the most expensive restaurants in the area because a comparative restaurant in the states would be way more expensive.

She also had a massive inheritance. She doesn't have access to it till she's 35, but he used to tell me he was so bitter that he would probably have to work his whole life until he was dead and would probably never make enough to really retire whereas she could basically stop working at 35 if she wanted.

They dated for 4 years, but it eventually fell apart.

- PleasantSalad

Wealth Whispers


I dated a pretty rich girl. Her dad was a prominent lawyer, her mom a successful artist, and her uncle was a 1980's pop star. Honestly? They were great people to be around. They were old money and not snotty or overly pretentious. Yes they had a big ass old house and drove quality (not overly flashy) cars. Yes they had whatever they wanted but not at all in a "look at me" type way. I on the other hand was DIRT POOR!!! I mean in the early 90's grunge was a blessing for me because I looked like that already. But her parents didn't care and we're always very welcoming. Her mom even took me to my first punk show. I guess it's true when they say cash screams and wealth whispers.

- PforPanchetta511

Little Acts Of Negligence

For me it was the little acts of negligence and damage that would cost money, but could be prevented. She would say "We'll call someone to fix it" but that person in my world was me. Which meant an hour of watching YouTube videos and a trip to the hardware store.

Every time she slammed shut a silverware drawer it made me wince. Doesn't matter that we both have good salaries... no way am I calling someone to charge me $250 for a minor fix.

- seppo2015

Crisis Mode

I dated a girl from a wealthy family when I was in college and I was very poor. The most frustrating thing for me was that our definition of a crisis was so different. From month to month I would literally not know whether I could afford my rent or be able to put gas in my car and she would be freaking out about some (to me) minor social issue or whether a store carried a fashion brand she liked.

It definitely made things difficult and I had to remember that it's your perspective that dictates what is a crisis and what isn't. It was honestly a lesson I've tried to remember over the years.

Joe And Sarah

Let me tell a story that I think will provide a nice contrast to the majority of the comments here... this story isn't mine, but that of a close friends'.

So Joe went away to college and met Sarah there halfway through freshman year. They were on-again-off-again for a while before deciding to date seriously in junior year. They met each others families during breaks or visit days at school. By all accounts, Sarah's family was polite and nice and relatively laid back. Not a whiff of arrogance or anything like that.

Fast forward to the end of senior year. Joe's paternal grandfather is on his deathbed and Joe desperately wants to go say goodbye. However, they go to school in a small town with a private airport (think Cessnas) and the closest major airport is several hours away by car. Neither Joe or Sarah has a car and the big airport didn't have a direct flight, so it would have been pushing 24 hours until he got to the hospice center to see his grandfather. This was destroying Joe, as he and grandpa were very close and he was essentially a second father to him.

Without a word, Sarah pulled Joe into a cab and took him to the airport. Waiting for them was Sarah's families' private plane. Joe and his family were all astounded. They had NO idea Sarah's family was wealthy, and especially not private plane wealthy.

Anyways, off Joe went. He was able to say his goodbyes and he flew coach back to school. Sarah never said a word about it one way or the other and neither did Joe.

They are now married and both doing well in their careers, and from what I can tell live a very normal life. But every once in a while they disappear off to some remote island or jungle or mountain for a few days and don't tell anyone but their family where they're going.

- DreamsOfGreen

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It's just designed to" look" easy only to bamboozle us.

Approach everything as a burden and live by a motto...

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