Men Reveal The Struggles Of Dating A Wealthy Woman

Some people are born into families with healthy financial resources. Others “make it” on their own. But one way or another, there are times when romantic relationships form between two people who don’t share the same financial status. And when this happens, some interesting developments have the possibility of coming to light…

A group of brave men have stepped forward to dish some truth about the times they’ve been with women who were a pay-grade above theirs, and how they felt about that financial disparity. They talk about how the relationship went, and most importantly, the biggest challenges they faced while in the relationship. These stories reveal the struggles men have faced when dating wealthy women…

To Move Or Not To Move?

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 into it.

But my friend had a job and life that he liked, and she was a stay-at-home mom. After a few years, it caused so much tension that their relationship ended. He’s done for, because they said if he tries to do anything legal, they will bury him. Now he has to drive three hours just to see his daughter. Reddit user: escloflowne

Social Security Checks

I dated this girl while in college. She never mentioned anything about her family’s money and lived a simple life until I went to her family’s place for Thanksgiving. Right off the bat, her mom didn’t like me. I respect everyone, but if you try me, I go very hard.

Her mom told me that she would feel more comfortable if she had my social security number so she could make sure I wasn’t a felon. I asked her for her social security number to make sure her money was legit and so that if her daughter and I had kids, they wouldn’t end up having grandparents in jail. We’re no longer together. Reddit user: iamfromouterspace

Two Different Worlds

Keeping up with their lifestyle and her expectations killed our relationship. She was constantly Instagramming her new Chanel bag that daddy bought her or her Gucci slippers, because that’s a thing for some reason. She would go on impromptu trips across the world every month while the rest of us had jobs.

She had a fantastically expensive apartment in the heart of NYC (that daddy bought) and would show up to every show and every upscale restaurant. As someone with a mundane job, coming from a working-class family, it was just too much to handle. We came from two different worlds, and there was no way we could exist together without one or the other being disappointed. Reddit user: cjinl

The Thing About Rich Friends

I dated an extremely down to earth girl whose dad had sold his company for $50 million. Our main issue ended up being that her friends were extremely judgmental of me. I had a very different outlook on life than they did, especially since I was a middle-class California kid and they were rich east coast kids.

They’d constantly complain about me behind her back because I’d call them out on things like treating wait staff poorly or just being obnoxious in public areas. I ended up having to break up with her because I got sick of hearing how poorly her friends thought of me. Reddit user: robswins

Being Rich vs. Coming From Money

Dating a girl who’s rich is different than dating one that comes from money. Once, I dated a wealthy older woman, and she insisted on paying when going out to dinner because she knew I was in college. I also dated one who came from money and who insisted on eating out but never offered to help out with the check.

She broke it off after the two consecutive date nights we spent at my apartment where I cooked dinner and we watched a movie instead of going out and going to a theater. I lucked out. Reddit user: vtzan

It Was Too Improper

I had a friend who dated a girl whose family was very well off. She was actively encouraged by her parents to break off their relationship. Despite my friend aspiring to be a doctor (he was well on his way, actually), he wasn’t from money, so they saw him as an “improper” suitor for their daughter.

I felt like I was watching a cheap romance movie story unfold. They dated for about eight months before he got sick of fighting for her parents’ approval. Reddit user: Luke5119

Too Out Of Touch

I dated a girl in college that came from a VERY wealthy family; like, she flew from Dallas to Florida (where we went to school) in her daddy’s business jet sort of rich. I think the biggest thing for me was how out of touch she was with everyday money issues and maybe a little bit of reality too.

For example, someone smashed into my car in the parking lot, and I was totally upset about it. She was like, “It’s ok. You can just get a new one!” She had no concept of how insurance or deductibles worked, and she didn’t understand that I could not simply go out and get it fixed right away.

Another time was when she wanted me to go to Miami to see a U2 concert with her. I couldn’t go because I had to work, and she didn’t understand that my boss wouldn’t care about how cool it would be to see U2. Reddit user:  SethRogen-Not

My Too-Simple Life

My girl had no self-realization of our financial differences and how it meant experiences in our lives were drastically different. She lived in Texas and would fly to NYC for the weekend, or she’d go to Hawaii, California, or Florida on a whim. And it would always be in first-class or a private jet.

When she asked me what I wanted, I was always really meager because that’s how I lived. I don’t need the most expensive item, but for her, it was all or nothing. Eventually, she learned to respect and almost envy my way of living. She enjoyed my simple life, but she ended up being a total sociopath.

When people weren’t gifting her things, she would just use her daddy’s black credit card to get it. She was a very selfish woman. I’m happy I saw the light. Reddit user: xccoaster

Perspective Dictates The Crisis

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. Month to month I would literally not know whether I could afford my rent or be able to put gas in my car.

She, on the other hand, 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 a crisis is and what isn’t. Reddit user: Supreme0verl0rd

No Life Experience

She was always doing something. Constantly going on trips, or to the openings of expensive restaurants, or traveling to her parents’ vacation house, or getting tickets for some opening night, or SOMETHING. It was frankly exhausting. She “had” money and she wanted to spend it, and I just couldn’t keep up.

I say “had” because it was entirely her parents’ money; she was in grad school (though she was struggling at it) and otherwise had absolutely no work or experience. Outside of a restaurant, she barely had any life experience either. Reddit user: lilSfish

$20 And The Landlord

She didn’t understand what it’s like to be broke. I grew up on welfare. I dated a girl in university whose father owned a multi-million-dollar company. At one point I was down to my last $20, trying to make it stretch until my next student loan deposit. I was at a party with our friends, and they offered me their drinks.

I took my last $20, went up the block, bought a couple of pizzas, and that was my contribution. I thought that was the least I could do, let alone the fact that, with my last $20, you can bet your last penny that I’m going to enjoy it with my friends.

She told me, “You don’t have to buy friends…and it’s pretty irresponsible to spend that money when you have to pay rent in a week.” Yeah, like $20 is going to hold off the landlord. Reddit user: 0xD153A53

Royal Obligations

This is about one of my dad’s mates. I don’t know all the details, but basically, he met a really nice girl who loved skiing. He loved all kinds of extreme sports, so this was right up his alley. He realized she was pretty wealthy after hearing about her regular holidays in the Alps.

Later, he found out her dad was the person who sits with the queen when she sits in her carriage and waves to crowds. Now when the dad’s busy, they’re expected to travel overseas and represent her father. And they have an obligation to write the royal family Christmas cards every year.  If I were him, I’d be looking for a divorce. Reddit user: BiggerBadgers

Minor Fixes And Annoyances

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. It doesn’t matter that we both have good salaries, no way am I calling someone to charge me $250 for a minor fix. Reddit user: seppo2015

Not The Right Fit

She was spoiled, and I couldn’t afford to spend the thousands a month in overhead eating out, going out, etc., at the time. I still did spend a ton, including $1000 on concert tickets for a show she really wanted to go to (they weren’t even great seats). But that wasn’t the half of our problems.

She got really upset that I wanted to stay in and cook once in a while. We fought over money a lot. Eventually, we broke up, and I’m really glad we did. Like unbelievably happy. I hope she is too. We were definitely not the right fit, especially when it came to her money.

Even though I love traveling, going to shows, drinking, and eating out (I do all of these a LOT), paying double and upping the base price was a very poor financial road map. Reddit user: JPSE

No Alone Time In Her Mansion

I once dated a girl who lived in Beverly Glen, near Bel Air. I lived in Canoga Park at the time, down in the valley. She would come down the hill, and I’d take the bus to meet her in Sherman Oaks. I really thought we would go the distance, but that wasn’t the case.

The biggest struggle was getting some alone time at her house, with her house manager, parents’ assistant, and caretaker around at all times. This was when I was 17; it lasted for almost a year, then she had to go to college- Syracuse, if I recall correctly. She probably ended up with someone more in her financial “class,” I’m guessing. Reddit user: UnderwaterPianos

Not Doing Enough

She thought her parents’ money was her money. Her parents would even remind her that it wasn’t. She literally got everything she wanted though. And one of the craziest things she asked for and received was a professional full format Epson printer. The thing was the size of a mini cooper and made absolutely stunning prints.

She also expected everything to be paid for. She also didn’t have to work, had school paid in full (we both went to Art Center in Pasadena, very expensive), so she had no debt. I’m still paying for it, and she had the nerve to tell me I wasn’t doing enough while I was going to school and working full time. Reddit user: Shpeple

High Expectations

I was raised in a family that made just enough money to keep a roof over our heads and food in our stomachs.  For me, the hardest part was proving my worth to her family. She admitted to me that her father told her that he thought I’d peaked as far income goes.

I just graduated in May. What? He also said that I will never be able to provide for her like an Ivy League boy coming from a successful family would. My goal is to prove him wrong, but I feel like I shouldn’t have to worry about that. Either way, that comment dug deep but motivated me if anything else.

Also, we spend a lot of time away from each other, because her family is always taking her on extravagant international trips for months at a time. Reddit user: Rofl_House217

Not Understanding The Struggle

They live in a bubble sometimes. They sometimes don’t understand the struggle of even the middle class. My girlfriend doesn’t ask her dad for money. But occasionally, if she needs something, she can ask. Her education will be paid for. And she says you should only have one or two kids or else you can’t afford their education.

She doesn’t understand that my parents can’t afford even one kid’s education. Yes, my parents did alright, but they can’t pay for my entire education. A discussion we have is that she sometimes doesn’t understand that she’s well off. Reddit user: ThePunisherMax

Eyes Wide Open

I dated two rich girls. They didn’t understand how other people can struggle in life. If I said I couldn’t do something due to finances, they got upset and would pretend it wasn’t about money. I don’t know if it was because they were rich, but as soon as they didn’t get their way, it was really bad.

My ex showed up at the busiest time of work, without warning, and just begged for me to go to lunch even though the line was out the door. Eventually, my manager got tired of her and told me to be quick. I felt super disrespected, and that opened my eyes to what type of person she is. Reddit user: kingkalis

A Lack Of Sensitivity

Their lack of sensitivity to prices. I was a grad student at a private university dating an undergrad. So, her family was loaded, and I was making like 18k a year. We go to a restaurant (she’d always pick nice places), and boom, appetizer, drinks, most expensive thing on the menu.

And without even a second thought. Not maliciously, but just because that’s what she wanted. But then, since I’m the guy, I’d pay. Like, hey, I have $25 a week for groceries, what are you doing? Reddit user: [redacted]

Finally Getting It

Their view of debt. I’m gearing up to ask my future in-laws for their blessing, and I know this will come up. No credit cards, no car loans, as they’re both of the opinion that no one should ever take on debt for any reason. Absolutely no student loans, and, unbelievably, NO HOUSE LOAN.

They have seven mansions on three different continents, and they’ve paid for all of it in cash. They don’t understand middle- or lower-class financial standing. Which is baffling to me, because her dad grew up very very poor. Being out on her own now, my girlfriend is starting to get it. Reddit user: tsimneej

Not On The Same Level

It was like starting a co-op RPG with someone who was already level 99. She wasn’t bound by the same limitations and constraints as me (or anyone else). She didn’t have to make a compromise, commitment, or sacrifice to get the things she wanted or needed. At all, ever, or this far in her life.

Her whole outlook was colored by the freedom of having this omnipresent safety net, so she never had to think too hard about the consequences of her choices. As much as I loved her, it would have ruined me trying to keep up. Reddit user: StanLDN

She Wanted Too Much Change

I dated one for a while, and it got super serious. Her dad was a big-time lawyer. I’m a photographer/musician who surfs and rides motorcycles, I also made tacos professionally for a bit. When I met her parents, she told me not to talk about any of this. I told her parents all about myself, and they ended up loving me (to her surprise).

She didn’t like that. I wear board shorts and flip flops to almost everything. For Christmas, she bought me all J crew clothes and told me to ditch the flip flops. She made more than me and brought it up quite a bit. All of her friends loved me though, and I honestly loved her too.

I treated her like a princess, but it just wasn’t meant to be. She once asked me how much I would get for my motorcycle if I sold it to buy her a ring. We broke up after that. Reddit user: Mikey_dude

Married To One

I married one of those rich girls. This may sound crazy, but the hardest thing I’ve had to accept is getting gifted money. It sounds great, but a lot of times there are strings attached to it. They constantly pressure her about moving home or give her grief over what we spend money on.

Everything is scrutinized, like where we go on vacation, what our kids do or eat, or where they go to daycare, what cars we have, etc. Also, there’s the societal norm that the man is supposed to provide for his family, and taking a “hand out” can be a really big ego bruiser.

It makes me hesitant to take anything from them. I guess I’d rather be struggling financially but have full autonomy over my life than being financially well off and losing some of that freedom. Reddit user: bigguynak

The Ease Of Travel

My ex’s family is extremely wealthy, and she just couldn’t seem to wrap her mind around people not being able to travel around the world when they’re in or right after college. She would ask why they don’t just work simple jobs to pay for their trips, not taking into account student loans and the anxiousness/necessity to start your career ASAP.

She was really modest and sweet and honestly seemed to resent her own wealth, but she just never experienced financial-based restrictions on her activities. Reddit user: milk_the_ham

Trying To Meet Expectations

I’m not sure how to put this the right way. The relationship between you and the girl’s parents mattered more than you and the girl. You would do things to impress her parents, not the girl. You were expected to graduate from the finest colleges, land a corporate job, or own a million-dollar business.

It doesn’t usually end well. I wouldn’t say that doesn’t last long; it could, but there’s definitely an end. But hey, not everyone’s the same. But super-rich usually are! By the way, my super-rich ex-girlfriend is a gem and very modest. But her parents caused trouble, and I just didn’t want to go through it. Reddit user: Suyogya17

Family Threats

I dated a girl 10 years ago; she was from China. She was going to school here and working part-time. She lived in a modest apartment and had a roommate. She told her parents that she loved me, and they didn’t care too much for that. They told her that they would disown her.

Her grandmother even said that she would die and it would be her fault if she didn’t break up with me. I know she wore nice clothing and always had lots of cash if we went places, but I would pay 100% of the time. We broke up because I didn’t want to get in the way of her family.

It hurt a lot, and I thought it was cultural or something. Then I found out later that they were Chinese rich and didn’t want white trash to ruin their daughter. I had no clue she was wealthy at all. Reddit user: r0botchild

That She Has To Pay For Things

Getting it through your head that she knows she has a lot more money than you, that she knows that if she wants to take you with her on the things she likes to do she will have to pay for everything, and that she knew that before she invited you.

She could take anyone she wanted on her adventures, but she chose you because she enjoys your company, thinks you will be fun, and that you won’t bore her with constant reminders of what things cost. Reddit user: MotorCityRacing

Living The Struggle

Her parents bought her a decked-out Mercedes G Wagon for her 18th birthday, and she had a trust fund that fully covered her college tuition…but anyone with a scholarship she scrutinized. She had been sheltered her entire life and complained about any minor inconvenience, and with anything serious, she couldn’t function and broke down.

I wasn’t poor; I was in the middle of middle class, but I had lived “the struggle” by that point and had a not so ideal upbringing.  She didn’t have thick skin of any kind. Reddit user: AmmoTuff182

Rich People Problems

Trying to empathize with their misfortunes. Dated a girl freshman year in college who was upset her parents limited her to only $1000 a month spending money. They paid for her meal plan, housing, and college already. She was also very upset that they were moving from a 1.3-million-dollar home to a 5.6-million-dollar home.

It was because it would be too big and they would have to hire more help, and she didn’t want any new ones. The biggest annoyance to me though was rude waitresses at restaurants (she wasn’t rude, the workers were). She was used to expensive food, and I was a broke college kid.

So if we went out to a nice steakhouse, she would pay. So many waitresses would make rude comments about it, and this resulted in petty revenge with low tips. Reddit user: Cupric_Sulfate

Once The Thrill Wore Off

I dated a subordinate at work that came from a very well-to-do family. They had two beach houses. She got $10k from ger granddad on her 18th birthday, and her dad was going to loan her $300k to invest in real estate…that type of rich. Anyway, things like that were commonplace for her, and I couldn’t wrap my head around it.

She would call things “cheap” that I actually thought were quite nice. It was a legit culture clash (she was also much younger, and we came from different races). I used to tell her that once the thrill was gone that she was going to settle down with a nice Jewish doctor…and that, folks, is exactly what she did. Reddit user: daveypop75

What Good Men Do

Oh boy. I dated a SUPER rich girl for about 8 months. Well, she came from a family that was utterly loaded ($100M+) and was “working” for her father’s company, earning a pleasant 6-figure salary with regular cash gifts from parents. It was the most expensive 8 months of my life.

She had super expensive tastes and expected me to pick up the tab for everything “because that’s what good men are supposed to do.” Only the best restaurants, hotels, rental cars, etc. That sucking noise you hear? Yeah, that’s my bank account…or what was left. And then she dumped me. What a fool I was. Reddit user: Tugford

An Unexpected Turn

I dated a girl whose family owned a major business in the city I lived in. I gave her everything I knew how to give, but somehow it still didn’t feel like enough. We tried to have a simple life, but her sense of worth was tied to possessions and money.

I wish I was making this up, but when she faced the idea of moving out of her dad’s house and making her own living, she took a job as a call girl. When her father found $10,000 cash in her room along with paperwork detailing her job, he threw her out of the house. Reddit user: [redacted]

Forgetting A Few Things

I knew a guy who dated a girl whose family was loaded. Apparently nice people but very out of touch with what “normal” people can do, financially, that is. They would do stuff like just randomly decide to go to the Bahamas or whatever and had trouble remembering a few things.

One, that he couldn’t just put it on his card, and two, he actually had work and couldn’t call out at the last minute. That’s not why they broke up, but it was apparently kinda uncomfortable. Reddit user: illy-chan

Too Much Pettiness

I dated a girl whose dad is a CEO of some huge company. She would fly to New York/California on a private jet every month, and she would spend $20,000 on clothes and jewelry. It didn’t last long, because her biggest problem was that her mom was almost spending more money on their dog than her.

I had college and a job to worry about, and I couldn’t take the pettiness any longer. Oh yeah, and she had a 200-foot yacht, and she would complain how boring the Caribbean was. Reddit user: IfTimeCouldDie

The Balancing Act

Her not being able to understand or at least fully empathize with financial struggles. One of my exes from college has a crazy wealthy dad. To this day (she’s been graduated for years now), he still pays her phone bill, car insurance, paid for the car too, and gives her absurd “gifts” in the form of cash seemingly randomly.

Back in college, she couldn’t understand why I was having anxiety attacks about balancing my life at the time, which included my job, school, and somehow being able to afford to live from month to month. Her attitude was “Oh my gosh, you just worry so much. Come on, let’s go have fun tonight….”

Uhh, I have to be up at 8 for a big test. Then I have class all day, and then I have to go work all night where I barely make enough to feed myself and pay bills. Reddit user: JohnyUtah_

Not Willing To Bear The Burden

I suppose this is more personal, but my girlfriend and I were long-distance, and she kept offering to pay for my flights as long as I kept coming to see her. She didn’t care about the money, she just wanted to see me, because she truly and genuinely loved me.

I know I wouldn’t have officially owed her anything, but it was an emotional burden I wasn’t willing to bear and so that, among other reasons, was a big factor in why we broke up. On the flip side, she had a ridiculously nice Audi and hated driving. So that was always fun. Reddit user: theogsamcam

An Overall Lack Of Appreciation

Relating on an economical level was tough for me. When I dated a very rich girl, she was never concerned about her future because it was always going to be taken care of. The lack of grit they have to work towards something as simple as affording a concert ticket. Instead, it’s just simply asking, “Hey mom/dad, can I have….”

Then that led to an unreachable standard for surprises, gifts, and just an overall lack of appreciation for the small (and what I would consider big) things I did to attempt to make her constantly happy/excited in a relationship. Reddit user: NotAtWerk

The Shallow, Vapid, And Self-Absorbed World

The largest struggle is resigning yourself to the second best where someone values money more than people. You’re stuck with that shallow, vapid, self-absorbed person in that shallow, vapid, self-absorbed social circle. You’re trapped. There’s little meaning. It’s all superficial fluff.

Worse, mental problems tend to increase with money, and it’s really hard to be empathetic when you see how the money is spent and thrown around. She might be hot, she might have a lot of flashy things, but in the end, you’re stuck with a sub-par human being on the decency level.

There are exceptions, but the trend is troubling. Women who come from limited means tend to find spiritual value and value in basic human interaction, and in the end, they make a better life partner. Reddit user: Lepew1

The Military Wasn’t Good Enough

My relationship with a rich girl lasted five years. And for five years, her parents hated me because I was, at the time, in the military, and that wasn’t good enough for them (because fighting for their safety and that of my country was not at all commendable). They wanted her to date an elite like them. What a nightmare, man.

I became an LEO here in Canada, and unlike the States, we make six figures; even then, that wasn’t enough. Eventually, they manipulated her enough that she ran off to Europe, and just left me out of the blue. Five years wasted. Can you really blame me for still being hurt and upset? Reddit user: Canadian-shill-bot