Regular Guys Reveal 40 Reasons Why Dating a Rich Girl Can be a Struggle

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Sometimes in life, we meet and date people who didn’t exactly grow up the way we did. Sometimes, we end up with people who can afford things we never dreamed of and for some men, it’s not exactly easy dating a rich girl. And they’ve shared their experiences with us in their stories.

From being threatened to being treated badly and not feeling like a man to not caring what anyone thought, we’ve got a full spectrum of experiences here for you today. If you’d like to see some of the things men have gone through when they dated or married a very rich girl, keep reading.

40. I Messed It Up

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My girlfriend and I 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 because she’s clumsy, but she was 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.

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She had more money and free time, her bucket list was completed by age 22. There was nothing new or fresh within my realm or ability. We got along great and I found out from a mutual friend that she was excited to be with someone not using her or groveling cause she was so rich. It was my pride that ruined it. 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 and I hope she’s doing well. She was awesome and deserves to be happy.

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39. Pre-Gaming Can Blow the Budget

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For me, the hard part was constantly balancing their lifestyle expectations with my salary. I went through it as a 23-year-old making $42k in Manhattan.

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A carefree weekend without pregaming can blow your entire monthly discretionary income.

38. Just Remember One Thing

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I learned one lesson from dating a rich girl: never marry a horse girl.

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You will always be third, after the horses, and her Daddy’s money.

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37. She Leaned On Me A Little Too Much

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My rich girlfriend expected me to be gentlemanly and pay for everything. She had the money and would do solo vacations (she didn’t work) then expect that for every day her kids were at their dad’s house, we’d go out to a fancy dinner or for drinks, and I should foot the bill.

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I grew up homeless and worked hard to make decent pay. Obviously, it didn’t last.

36. $12, 000 A Month

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I lived in a pretty rich area of the bay area. My girlfriend, at the time, was very rich in this already-wealthy area. But she truly had no concept of money.

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Her allowance was $12,000 a month and her family bought her a brand new Porsche because her car was a five-year-old BMW M5. It was honestly like dating an alien.

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35. Trying to Keep Up

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My roommate was very wealthy and her boyfriend ended up living with us for two years. I remember they would have the same fights all the time: he came from a very poor household, tough family life, in a not-so-great area, 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 wanted him to do more, be better, etc. But they also fought a lot over gifts; she would buy him really expensive gifts that he needed, but couldn’t afford to buy himself. A good coat and boots with one or two other items can easily get close to $500-600 and he could never get her a gift of such magnitude. He said he would dread holidays, Valentine’s Day and birthdays because he would get so stressed out trying to constantly think of creative ways to match her really expensive gifts.

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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. 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 four years, but it eventually fell apart.

34. A Game of Manipulation

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My girlfriend (now wife) wasn’t rich herself but had very rich parents. The toughest thing was that her parents would offer to pay for everything, but would later try to use that as leverage to control her when they didn’t like what she was doing. They would stop paying for her car suddenly or reneging on a trip that they offered to pay for. It was certainly toxic from their end, and she kept falling for it each time.

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However, in her 20s, once she was out of college and employed, she didn’t need their money, so anything that was offered with strings attached (or had the potential to do that), she could just decline. They learned pretty quickly that manipulation via finances isn’t a good way to foster a relationship with their daughter. Her mom figured it out; her dad not so much. For unrelated reasons, they got divorced, and her relationship is still very strained with her dad.

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33. His Hands Are Tied

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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.

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After a few years, it caused so much tension that their relationship ended and she moved into the house herself. He is screwed because they said if he tries to do anything legal that they will bury him. Now he has to drive three hours just to see his daughter.

32. Firing Right Back

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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 did not like me.

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I respect everyone, but if you try me, I go hard. Her mom told me that she would feel more comfortable if she had my social security to do a check on me, to make sure I was not a felon. I asked her for her social security to make sure her money was legit and that if her daughter and I had kids, they wouldn’t end up having grandparents in jail. We are no longer together.

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31. Rags To Riches to Rags Then Riches

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My buddy married a super rich girl from China. He grew up in the suburbs and came from an economically poor family. He went from rags to riches, having literally started from nothing. And he changed quite a bit. He went from having nothing that was branded, to suddenly having everything, including a brand new Porsche. He was outfitted with super expensive clothes, lost a bunch of weight and turned out pretty good for himself.

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He later discovered that his in-laws were just using him for immigration/business purposes since he’s American and he ended up divorcing his wife, having no kids. Half of nothing is, well, nothing. He got a divorce with the clothes on his back and his car (that he was given). Since the divorce, he got a high paying corporate job making six figures. He now has all his luxury goods and is currently dating someone who looks like a supermodel. And he still has his Porsche SUV.

30. Breaking the Bank

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My husband’s work colleague currently has an issue in picking engagement rings.

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The cheapest one she wants is $17000; he makes $25000 a year.

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29. Admitting the Struggle

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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, they led me to a room with three types of new clothes, 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.

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Managing expectations of my wife for travel and expectations with children’s activities was difficult; 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.

28. She Left Me For A Guy Who Could

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My rich girlfriend 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.

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I couldn’t just fly to the Caribbean at the drop of a hat, so she left me for a guy who could.

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27. Not Good At Being Political

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I dated a senator’s daughter in high school. Everything was about keeping up appearances and we had to be careful where we went in public and stuff like that.

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Her parents offered to get nicer clothes to wear when we went to dinner in public, but I felt weird about it. The relationship didn’t last long;  I’m not good at being political.

26. The God-Awful and Judgey Mother-in-Law

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Mine was just a girlfriend, but her mother was God awful. She was judgemental, pushy, would trash talk the poor not knowing I was from a poor family. 

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Her dad, who was the breadwinner, (her mom hadn’t worked in her life) was such an awesome guy. People like her are trashy- she rides coattails and thought she DESERVED all the pride and respect that her husband got.

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25. The Insensitive Girlfriend

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My girlfriend grew up pretty well off and developed some expensive habits and tastes. When we first started dating, she was okay with eating at Chick-Fil-A and restaurants of the sort, but as time went on, she started to refuse going there and wanted to go out to “better places.”

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There was one night where she was going to cook dinner before we went out for the night. She messed up the recipe a bit and tossed the whole meal in the trash and said we could just go eat out somewhere. I was panicked inside money was low and I didn’t know how I would pay for gas or rent until I got paid again. I threw out suggestions for things I could afford like pizza, chicken, or Mexican food, but she and her sister decided they wanted to go to this upscale steakhouse. We went there and she and her sister both had $35 meals; I didn’t order anything and just said I was feeling sick and not hungry. I don’t know if she fully grasped the concept of bills and how expensive they can be.

24. No Problems

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I married way up and live in a nice medium-sized city. The main road, the mall, the parks, schools are all named after my wife’s family. When my mother-in-law goes out with us to nice restaurants, everything comes to a halt. People whisper and it’s a surreal existence sometimes.

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I’ve got a good job (unrelated to her family) that takes me out of state pretty often, but I really don’t have to work, although I feel too young to retire. I didn’t really have any struggles dating my wife since she’s very down to earth. Her family was/is very gracious and I never felt weird. I’m often referred to as Mr. HerMaidenLastName, and I’ve never minded. I figure it’s like being the non-famous spouse of a famous actress.

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23. Gifts All the Time

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In my experience, gifts seemed to be the language of love, both giving and receiving. She would buy me things and tell me how much I meant to her and she expected the same in return. I was by no means poor, but my father believed in a strong work ethic and taught money management; when I went to college, he only paid tuition and said I had to pay for everything else. I learned a minimum wage job makes just enough for a roof and ramen. She didn’t understand that I couldn’t afford gifts all the time.

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Not being able to take her out to eat, to the movies, out on the town on a weekly basis was a big deal. At the same time, I couldn’t blame her; it was how her family communicated their feelings. We were both young and hadn’t lived life yet. I haven’t talked to her in almost 15 years. I really hope she has learned that love is not a gift purchased, but something conveyed through speech and actions.

22. Putting Up A Fight

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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 wasn’t from money, so they saw him as an “improper” suitor for their daughter.

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

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21. A Happy Ending

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My partner’s parents bought us a house so we could rent to own it from them because we were having difficulty where we were.

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They really put a lot of thought into the location and amount of effort needed and everything. We are all very happy- I finally get to experience parental figures who are nice to me and don’t expect a lot of emotional labor.

20. Paris or My House

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My rich girlfriend was really nice and we had fun, but there just came times where she could either stay at my house in Ohio for the weekend or go to Paris for a few days with her family.

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After a while, it got to where she didn’t stay at my house at all.

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19. Too Tired to Care About Which Fork to Use

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Learning the silverware, table manners, and new social behaviors were the biggest challenge for me.

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I had to explain to them that it’s not that poor people are uncivilized, it’s that they are too tired to care about what fork to use; they are just happy to have food.

18. No Way to Exist Together

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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.

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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.

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17. She Was Perfect Otherwise

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I’m a lower-middle-class Mexican guy. My girlfriend was Indian and her family’s household income was around $400,000 a year. This girl grew up in Dubai, taking swimming lessons from Olympic coaches; she had never experienced any struggle. Our biggest arguments were about how I needed to get a master’s in a lucrative career that could keep her in the late she had become accustomed. And we also fought because she didn’t understand how circumstances could leave people in cycles of poverty.

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She really believed there were no excuses; she thought homeless people and poor people should just try harder and go to college to get better jobs. We ended up breaking up because as a non-Indian/non-white person, I would have needed at least a master’s degree in a lucrative career in order to meet her family. It killed me because her personality was otherwise perfect. But after that breakup, I felt worthless for years, like I wasn’t good enough for anyone.

16. Too Many Rich Friends

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I dated an extremely down to earth girl whose dad had sold his company for $50mil. 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.

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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.

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15. Making “Us” Look Good

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I’m married to a rich girl. I invested what little I had into a business that no one had thought of before and it’s now booming today. It’s hard that what I make in a week at my regular job, she can easily make in about an hour. When she wants to go shopping, I want to be the man who pays for everything and make it look like I’m a provider, but that’s not the case at all. So she got me a debit card from her bank, in my name, and I pay with that to make us look good (we live in an area where it’s customary to have the man pay and provide).

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All around, it’s great because I now have access to a part of life I didn’t before. Traveling is fun, modifying cars is fun, racing is fun, staying in hotels is fun, and just having the ability to spend over a hundred dollars without having a panic attack about finances is a lot of fun.

14. Different Kinds of Rich Girlfriends

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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.

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I also dated one who came from money, 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.

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13. Returning the Favor

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When I met my wife’s parents, we went out to dinner. Toward the end of the meal, I excused myself and went up to the hostess and asked for the check so I could pay it.

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Her father sprinted across the restaurant to stop me from paying. For Christmas, I got him a gift certificate for that same restaurant. It’s a running joke now.

12. Out of Touch with Reality

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

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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 would not give a shit about how cool it would be to see U2.

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11. They Don’t Act Rich

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My wife didn’t tell me about any of the money stuff until right before we got married. I knew that her family was pretty well off because I had traveled with them a few times, but I honestly had no clue what it was all like.

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We only live off of what we make now, any money in any other accounts are for very specific purposes (down payment for a house, car savings). I feel very fortunate that I married into a family that knows the right way to handle money and doesn’t act rich.

10. She Understood, But She Was Selfish

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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. 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.

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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.

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9. No Money, No Problem

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There was literally nothing wrong with dating a rich girl, just like I did when I was poor, back in college. I had a good major, was an athlete, and her family loved me. I didn’t have money to give her flashy gifts, and she didn’t care. If she wanted a Birken, she’d just shop with her mom. I didn’t have money to take her on fancy vacations or trips; we’d just go skiing at her parents’ condo and I could always find a way to scrape up some money to get myself there and everything else would be taken care of.

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They didn’t care that I wasn’t “an appropriate” suitor at the time; I was just a college kid and must have done a nice enough job of presenting myself that they knew I’d figure it out. It was an awesome relationship- one of the least stressful imaginable. We eventually fell out of love for other reasons, but I look back on that time fondly and we ended things amicably. I’m still on good terms with the family too.

8. The Constant Reminder

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My girlfriend was always reminding me of how much money she and her family had.

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I consistently reminded her that I didn’t care and that wasn’t the reason I was dating her.

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7. Playing the Game

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My girlfriend was extremely rich and each time we’d go out, she’d pay.

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Just so I wouldn’t feel bad or look like a total user, I’d pretend to pull out my wallet when it was time to pay and ask, “Are you sure?” before she took care of it.

6. Different Priorities

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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, and she would be freaking out about some (to me) minor social issue or whether a store carried a fashion brand she liked.

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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. It was honestly a lesson I’ve tried to remember over the years.

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5. Just Roll With It

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I was going to a family wedding with my then-girlfriend/now-wife- it was her cousin and his wife. My now-mother-in-law sent me a huge box full of really nice clothes to wear.

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I had mixed feelings at first; I’ve always been kind of perpetually a free T-shirt wearing kind of guy. I rolled with it and things are great!

4. Rich and Dirt Poor

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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 old house and drove quality (not overly flashy) cars. And yes, they had whatever they wanted but not at all in a “look at me” type of way.

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I, on the other hand, was DIRT POOR!!! In the early ’90s, 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.

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3. Not A Terrible Problem to Have

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We’re both professionals and doing pretty well by most standards, but our fairly quiet/comfortable life is still different from how she was raised. Our in-laws have several international properties, so we can afford to travel by visiting the same places and staying at their places. It doesn’t feel too weird now being around her family; we have several kids, so that’s the focus of get-togethers.

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I am treated well and they are genuinely nice people. We have had to ask them to tone down Christmases for our kids and they’ve been respectful of that (their gifts were dwarfing ours) – but again, that’s not a terrible problem to have.

2. Role Reversal

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I’m the opposite of most of the guys here. I grew up with less money than my girlfriend, but it mostly gave me a “screw it, money never lasts long might as well buy stuff that gives me some happiness” attitude.

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She’s the one who knows how to budget and save money.

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1. She Couldn’t Relate

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My girlfriend didn’t quite understand the strain of a work week, prioritizing bills, and also carried the guilt of having the money, which was frustrating.

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Our relationship didn’t last long for those reasons.

Hassan Washington

Hassan Washington

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