The Truth About Dating as a Single Rich Woman

woman in wetsuit

Photo by Marlene Leppänen on


I’m in my 30s, single and I have a high-paying job.

I didn’t mean for this to happen.

I never cared about marriage or starting a family. By default, I chose to focus on my life and career in my 20s. I think if I were going to do it again, it may have been easier to do family first and then career. Though it would seem that having a career and a high income would be an attractive asset in the dating world, I have found it to be more often a liability.

What I Mean When I Say I’m Rich

For some background, I live in DC, home to tens of thousands of interns, students, and federal government workers. In DC, lawyers make some of the highest salaries in the city (whereas in SF or NYC, say, tech founders, bankers and people in many different industries can make much more). What this means is that when I date, 9 times out of 10, I’m dating a man who makes less, often a lot less. As of late, I generally make 2-3x more than my date, but I’ve dated men with bigger income differentials (students).

Does my career/salary hurt the kinds of men that respond to me online? I have no idea. People don’t fill out questionnaires. I do know that the income differential has caused rifts in my relationships though. I still haven’t figured out how to navigate the issue of who pays. If I were a man dating a woman who made a quarter of my salary, I would pay for at least half, but more likely I would pay for most things. But as a woman, it’s less clear what my role is.

Entering Unchartered Pay Disparity Dating Territory

I remember I had a fight about money with my ex, who we shall call Bob. He brought up that I was contributing less than half toward our food budget. We never discussed our salaries but it was understood that I made considerably more than him. We were both earning good money though and neither of had debt or high expenses. Combined we were likely in the top 2% of incomes. We went to nice but not extravagant places.

A few weeks before the fight, I had actually thought about whether I was contributing my fair share. When Bob and I went out to eat, one person would pick up the tab. My family is Asian so splitting the bill is a bit foreign to me. I detested the idea of a couple keeping spreadsheets to ensure each side was paying exactly 50%. I was hoping for something easy-breezy and motivated by love (*in the future, maybe spreadsheets are the answer).

But I also thought about fairness. By my calculations, I paid for about 1/3 of the meals out and he paid 2/3. I also cooked often and would plan and shop for the meals. I would cook somewhat expensive or elaborate meals – slow-roasted pork belly, chicken pot pie, paella, baked salmon, pork loin banh mi, katsudon donburi. By my rough estimates, I figured I was paying for half our total meals (eating in and eating out) though I was spending less because cooking is cheaper than eating out.

He was resentful. And I was resentful that he was resentful. I felt like he didn’t recognize my efforts. Also, I was resentful because if I made less, this wouldn’t have been an issue. My cooking would have counted as my contribution towards our “couple-y” expenses. But because I made more, I should pay for more. It didn’t seem fair.

What is Fair in Love and War

Of course, I’m sure it was fair. If I were a man, I’d pay more. When I was younger and making an entry-level salary, I dated a lawyer.  He paid for most of our dates and he would cook as well. The tables had turned.  But I wasn’t ready to pay for more than my half.

Now in my 30s, I’m learning to acclimate myself to paying more. I feel that this is the right outcome. If I had married when I was younger, I wouldn’t be in the career I am now. Many of my ex-boyfriends made good money. I doubt I would have had the ambition to make more if I already had a good source of income (from my hypothetical hubby) to support me. I went to law school in a small town, and I’m not sure that many men would have followed me there. If I had had children, I would have taken a break from work and I’m not sure I would have returned.

Because I didn’t focus on family, I have a career. Because I have a career, I have a high-paying job. With that high-paying job comes certain responsibilities like paying for more. This is the price of change. I’m working on my resentment.

Why I’m Still Worried

A woman outearning her husband increases the couple’s likelihood of divorce. Being nominated for the Best Actress Oscar (a sign of a woman’s success over her male significant other) increases her risk of divorce. When a woman earns more, she might resent her husband for earning less. The pay differential may change their dynamic. Her husband might be jealous at her success. These are not great things, but they are natural things. You can be a part of a team and still be jealous of your overperforming teammate or resentful of your underperforming one. I’m sure the rest of the Cavaliers all envy LeBron and LeBron may get tired of carrying his teammates. We would like to think that this jealousy or resentment will stir in us ambition to greater self-improvement or empathy but for many, it’ll be corrosive.

I don’t feel ashamed that I will likely date and marry a man who earns significantly less than me. I would be lying, however, if I said that I don’t worry at all about ill effects due to outearning my spouse. I’m learning to get comfortable paying for more. He will have to get comfortable with me earning more. It’s a whole lot of uncomfortable. I guess that’s what happens when you buck societal expectations. It’s for the best, but it doesn’t feel that great when you’re learning to change. I think they’re called growing pains.

Some will say, oh it’s ok because the men who are uncomfortable with your success aren’t right for you. I think a lot of men are or would be uncomfortable with the success of their female significant other. Many men don’t have to deal with this scenario – as the typical case is still that the man earns more. But we live in a society where it’s expected that the man earns more. Men can brag about how happy they are to be kept husbands – but the fact that they can brag about that shows that that’s not the norm. It’s generally uncouth to brag. If a woman were to brag about being a trophy wife, she’d be derided if she wasn’t being sarcastic. Trophy husbands get the best of every world – they get to work less, brag about that fact, and get lauded for being supportive. Meanwhile the bread-winning wives are warned that their husbands will likely have an affair.

Most of the women I know are dating or are married to men who make more than them, often significantly so. It seems really stupid and backwards to want to feel like a princess who is funded by her prince. I will admit that I had had a little hope in the back of my mind that that would be the case for me. Maybe I could be Meghan Markle.

If this is a big problem? HELL, NO. If it were, I could just quit my job and become a receptionist. There are easy options to go from higher-earning to lower-earning. I realize that this is a great problem to have in some ways. I don’t have to rely on some rich man to pick me. I can support myself. I can be single if I want.

Turns out, in my own fairytale, I’m the prince. And I’m learning to be ok with that.


20 thoughts on “The Truth About Dating as a Single Rich Woman

  1. I agree that society has the expectations already set for us: men earn more and women earn less, and women take on the bulk of unpaid labour. Which is great if that works for you and you are happy to conform, but it leaves those who don’t want to conform like rich women and caring men as outsiders. And sadly we’ve not seen a great number of caring, non career minded men coming forward, but we are getting a lot of richer women.

    As for paying for dates; truthly I like cheaper dates, not a great fan of eating out anyway, so I don’t tend to have these issue. But it is something I’ve been thinking of, how comfortable would I be dating a man who earned significantly less? Would it be a dealbreaker, and if so is that horrendously hypocritical of me?

    Yet it seems much more acceptable for high earning men to date low earning women than vice – versa, so we’ll end up with an unbalanced society. Don’t they say we will have two left over populations: single rich women (who will be an asset to society, caring and consuming) and single poor uneducated men, who may cause trouble.

    1. I think a lot of people have come forward on Twitter to state that their marriages have been fine with a breadwinning wife. I do wonder if it changes if they’re in the same industry. Or if it changes over time or if it’s a great disparity. Most couples won’t have to deal with this problem though – only 1/3 of women make more than their male significant others now and most not significantly so.

      I don’t think it makes you hypocritical to eschew dating men who make significantly less. It’s just normal. And I guess we can’t really judge you till you get to that bridge =D – and it’s likely that there’ll be differences in personality, education or social circle that would be dealbreakers.

      “Don’t they say we will have two left over populations: single rich women (who will be an asset to society, caring and consuming) and single poor uneducated men, who may cause trouble.”

      This, on the nose. I’ve seen books and research saying that the answer lies with these two groups. Dating books say women need to date less educated men.

  2. Huh, being a man, I never really thought about the issues you brought up. My wife and I(late 40’s) have been married for 20 years and dated 5 years before that. She made more money than me at the time of dating and first 5 years of marriage. We now make about the same.

    We never fought over who makes more, who pays more. We did not live together before we married. One of us just picked up the bill and it worked out. Heck, we even split the cost of the engagement ring because she didn’t want me to dip into my savings since I was making less than her.

    When we got married, we combined our finances and went from there. It was never about who makes what and how much they can spend. Granted, neither one of us are big spenders. I guess we go lucky.

    1. It’s great that you are your wife haven’t faced this problem! My parents didn’t face this problem either but I’m not sure if my mother made more than my father.

  3. these are interesting topics. you certainly don’t want to end up being seen as a meal ticket. back in the day if i asked somebody out then i was paying. even if one side makes more it’s not about the math. i always found it a nice gesture if a girl/woman offered to pick up the occasional dating check, however small or large. the other nice thing is the offer of “let me take you out this time.” then it’s kind of understood.

    1. I think it was simpler back in the day. Now no one knows what they’re doing in dating! Thanks for sharing.

  4. Thought provoking. My wife Anna and I have been in both positions – I was making more than her before leaving my job, now she’s obviously making more than me. It will probably change back again if I go back to a position in my field, because my field is a higher paying field than hers. But if I instead give a freelancing-focused career a go of it, it will likely be awhile before I am making the same as her (or more).

    I personally have no issue with her being the breadwinner, now and in the future. That doesn’t mean I will make decisions based on who would be the breadwinner and what that would mean for the dynamic of our relationship. I would hope she doesn’t, either. For either of us, the biggest thing is that we are happy with what we are doing, and we are growing in ways we want to be growing. As long as we are financially stable, honestly the money stuff is just a byproduct.

    I think the big thing here is finding someone secure enough with themselves to be happy in either scenario. Unfortunately, the cultural norms we are surrounded with often dictate our level of security. Since it’s “normal” for men to be making more, it’s normal for them to be insecure if their wife/girlfriend is the breadwinner. So finding someone who can be more open minded in general, I think , is important.

    1. I agree – it’s about finding and being someone secure enough in either scenario. The problem is that sometimes the situation changes and while everyone thought they were secure, resentment springs up unexpectedly. This has happened to at least one of my friends. At least I know from the get-go if it’s a problem that I earn more.

  5. Another thought provoking post . I think most women who want to keep the family going won’t bring it up when they are making more and try to remind themselves it’s just temporarily . I’ve heard enough women openly admit after the spouse catches up reflect on the time when the female out earned the male and in retrospect it was “OK for a girl. .. But not great .”

    The dicier business is when the female brings in a much higher net worth while the guy is deep in debt. Usually it doesn’t work out.

    1. Totally agree that the discussion is totally different for a woman who makes more than a man. It’s all about lowering expectations.

      I’ll let you know how it turns out if I ever get married. 😂

  6. What will happen if you marry a man who’s making 1/3 what you are making and he’s fine with that and fine with you paying more (which you’ll have to unless you want to live a lifestyle that matches his salary) but he is not interested in domestic work/management? What if you are paying more, and he’s spending long hours at his job making chicken feed compared to your salary; meanwhile you are managing children and home. Say you hire a lot of it out, but you still manage it all and do more with the kids.

  7. We live in an age where women are able to work themselves up to be men’s equal and sometimes superior, such as your case since you’ve mentioned that you’ve had experiences with a ton of men who made less than you. But does that actually cause a problem? i do not think so, i believe that a man is ought to Applaud his wife/girlfriend for her achievements in her career, and take advantage of that and use it as a motivational cue to do better. Perhaps the person who you were with seemed somewhat ungrateful since you’ve cooked several dishes back home, a woman with a high-paying job such as yourself must be occupied with her work and yet you still cook at home. What does this indicate? This indicates that you’re showing domestic effort back home as much as you’re showing work effort out there in your field, this also indicates that you separate your work life from your domestic life back home which creates a comfortable aura for both couples. That being said, are there a lot of men who feel insecure or feel that their masculinity is at stake when you’re making more than them? There are some men who’re like that however, there are also men out there who seek for an equal partner in the upper middle class status that share independent thoughts, ambition, curiosity, knowledge, and much more in which you could relate to. Heck if you could relate to that man in one of these traits then that’ll be a good starter for both of you. Now i do not know if you believe that reddit could be a good source of evidence, but i’ve done my research there and found out that there are men who are in relationships with women that make more money than them and are in a whole different class, such as Upper middle class or Upper class. They feel uncomfortable however, they believe that they can achieve more and there is this one man that has grasped my attention, he married his wife who comes from an Upper class background however he didn’t complain, didn’t resent her, didn’t feel that his masculinity was at stake 24/7, didn’t waste his time thinking if she is better than him. He worked himself so that he could reach a significant class status in society and that being “Upper Middle Class” he had begun to start his own business and eventually bought a farm for himself and his wife. My personal opinion about this as a man? I feel like i’d be more happy to be with a woman who makes more money than me than with a woman who makes less money, because like i stated above it motivates me to do better, and i would never take advantage of her wealth or resent her for it. However i do share a “bitter” trait that she or anyone else may feel uncomfortable with, i am not the kind who would eat out, i rather eat in and enjoy good quality foods instead of eating out because i believe that you can never trust your restaurant’s kitchen no matter how rated the restaurant is, haha :p If my reply had changed your thoughts, then please do notify me. How did it change your thoughts and why? Do you believe that there are still a chance for men among your class status or below that may categorize your class status as a motivational cue? whatever would be appreciated, thank you for sharing this post in advance.

    1. I’m sure men could take my status as a motivational cue, but I don’t really need them to. I don’t really care if a man has more status than me, it’s more about whether he will be accepting of me. It’s not a huge problem, but it’s been more of a problem than I ever expected when I was young.

  8. I came from a low income background and by 30 was making a top 5% income. I met my husband after that. I loved that he was inspired by my story. He wasnt threatened by it like so many of the men I dated. He was inspired and motivated. Early in our marriage, he quit his job, deciding to pursue a PhD. He failed out of the program that the first year. That damaged his self esteem, but he stayed inspired and motivated. He went back to work in a new field, determined to earn a salary that could support me as well as I could support myself, should I decide I didn’t want to work anymore. He adored me, and I felt so loved. He worked at that job for several years, and the company took advantage of him. The wages were laughable for the industry/position, and the hours were absurd, especially considering the wages. But he strove on. For me. As the years wore on, I realized he was burning out and becoming frustrated and angry. I suggested he quit his job or at least set some limits with his company and see what happened – we had plenty of money. The suggestion was met with a hostility that took me by surprise. This was at least 3 years into our marriage. As the years wore on and he grew even more frustrated and angry, I tried hard to convince him that this wasn’t what I wanted. I married him because he was the lightness that contrasted my seriousness. He made me laugh and kept me balanced. That wasn’t who he wanted to be though. He had become hell bent on earning a salary comparable to mine, and I became the competition. Meanwhile, he had no time or attention for our home life. This became a very unpleasant life. Eventually though, he did get a windfall at work, and his salary approached 1/2 of mine. He was happier than he’d been in a long time. I was complaining that I didn’t want all the home life responsibilities. He was like “I did all this for you, and you’re complaining about dishes?” I was like, “Um no, you did all that for you. I never needed money. I need a partner at home.” Then I took another job that almost doubled my salary, and his self esteem hit the floor. Ever attempt I make to help boost his self esteem is completely transparent and only makes matters worse. My heart is broken, because for years I felt like I was at the center of his heart, and now he can’t see me through his defenses. He’s miserable, and even though he’s a wonderful person that I have a 10 year history with, I’m going to have to say goodbye.

    1. I’m so sorry to hear about your situation. You’re very much not alone in having to deal with the difficulties of being a higher-earning woman and you’ve done an admirable job throughout your relationship. Wishing you the best of luck now and for your future.

Leave a Reply