Why Successful Women Struggle in Dating (and How to Win)

single successful woman

High-achieving women often encounter a frustrating paradox: their success can feel like a roadblock to finding love.

And it’s not just anecdotal.
Studies show that high-status women are less likely to enjoy mating and reproductive success.

At The Power Moves, we’ve dedicated years to decoding dating dynamics, blending research, evolutionary psychology, and real-world experience.

In this article, we’ll explain this happens and share proven strategies to conquer the dating world without dimming your shine.

Why Successful Women Struggle

As it’s often the case, there are multiple contributing causes to complex social phenomena.

Let’s start with the major ones>

1. The Higher She Goes, The More Her Dating Pool Shrinks

Let’s start with the first, most obvious reason.

Women, more so than men, show a more or less marked tendency towards hypergamy, meaning that they prefer men who are “better” than they are.

This creates an obvious problem because the better she does in life, the fewer eligible men she will find who are at her level or above.
Paradoxically, average women have it easier than successful women.

Here’s a chart to clarify this concept:

chart of successful women dating options
Women want men who are ahead of them. So the farther she travels, the fewer the men

Women think that a big salary and a big-name college should increase their options, but sometimes the opposite is true.

Of course, we are talking here about preferences.
Women can physically reproduce with any functioning man, but dating less successful men feels like “settling” to most of them.

Where’s The Problem?

Unless you are well-versed in evolutionary psychology, you might miss the issue here.

You might think, OK, but men also must want equally successful women, so they just find each other.

Well, it’s not exactly like that:

2. Female Success Is Not As Attractive As Some Women Think

What? Men don’t like successful women?

It’s not that men don’t like successful women, but:

  1. Men have lower “success standards” than women
  2. Some traits men value can be antithetical to success (i.e., age, submissiveness, and a nurturing disposition)
  3. Men only value professional success up to a certain point (and almost never above their level)

Sure, men say they value intelligence and success, and nope, they would never be turned off or intimidated by it (a rational stance, BTW).
But what people say doesn’t always square off with what they do.

Despite what they say, men indeed prefer women who are “less” than they are:

  • Some men prefer less intelligent women

Studies show that above a certain threshold, men find female intelligence a turn-off.
And it’s especially when he feels that she outsmarts him that he really loses attraction (Park et al., 2015).
Evolutionary psychologist and researcher David Buss says that men who rated intelligent women highly for long-term attractiveness still rated them as low in sexual attractiveness.

  • Many men prefer less dominant women

Women prefer more dominant men, while men prefer more submissive women (Wu et al., 2016)

This is true also for some of the most successful men, which is why you see many tycoons with very low-key women (read: strong VS submissive women).

  • Men prefer women who earn less

Time and culture have changed, but people haven’t.

And deep down, most people don’t feel it’s OK for her to earn more (Bertrand, 2013).
That attitude translates into numbers, as statistics show that men tend to marry women who make less (or women marry men who make more if you prefer).

  • Men are wary of highly-ambitious women

Women like ambitious men, but men don’t award ambitious women any more points (Townsend, Wasserman, 1998).

As a matter of fact, ambition is often considered a masculine trait, and that’s probably why women hide their ambition (Harvard Business Review, 2004).
Women who do not hide their ambition can be seen as gender deviants and lose points (and that’s probably why Hillary Clinton lost the election).

  • Alpha men prefer kinder women

Finally, some alpha males prefer not to date “alpha females,” as that could mean more battles for relationship control and less mutual caring.

Successful men, work hard.
They might not want to admit it, but they prefer going home to a kind woman who helps them unwind rather than another (spent for the day) corporate fighter.

See Trump making this point:

Trump: It’s a bad idea to put your wife working for you (…) Ivana would get angry at someone working at the casino and she’d start shouting. And I’d say “I don’t want my wife shouting at someone like that”. There was a great softness to Ivana, and that softness disappeared. She became an executive and not a wife

That softness he’s talking about is femininity.
When Ivana started working, she started acting more aggressively, more like a man. And Trump’s attraction started vanishing.

Note:
Many dominant women turn submissive to more dominant men, but they still require more energy to “tame,” and that’s why men often prefer more submissive women to begin with.

3. High-Quality Men Have Options & Leverage

Here’s another dating woe for career women: high-quality men and women have totally different markets.

Why?
Because, as men and women go up the success ladder, their dating markets move in the opposite direction.

While women would rather not date less accomplished men, men are OK—and sometimes even prefer—dating and marrying women who are less accomplished than they are.

And if that weren’t enough, men have even laxer standards when it comes to short-term partners.

This creates huge imbalances in the upper echelons of social status.
Look at this chart:

bell curve chart of successful women and men dating options

Successful men have huge leverage, which leaves some career women frustrated when said men don’t chase and invest at all.
“Doesn’t he realize what a great catch I am”, they wonder-.

Well, as we have already mentioned, men don’t value their career achievements as much as they think.
And when men have options, their dating strategies often change.

Jon Berger in Date-Onomics explains that when women are abundant, many men go from monogamy to a “spread the semen far and wide” strategy.

4. There Is An Oversupply of High-Quality Women

There are no good men left
-the cliche’

But is it really a cliche?
Turns out… It isn’t.
At least not for successful women.
It is harder for a successful woman to find a man.

“Successful”, as much as ‘high-quality,” is partially subjective, of course.
But it’s less subjective than some sources would want you to believe. And women are kicking men’s asses in many of the areas that make a person high quality.

Including:

  • Women are more educated than men

Women have long overtaken men in obtaining college degrees, and the difference has kept growing over the years.

And since women have historically been reluctant to marry less-educated men, that’s a huge quality issue for successful women’s dating opportunities.

gender split in higher education

In recent years, women have been adapting (or settling?), but the highest rates of unmarried (and childless) women are still to be found among the most highly educated (Pew Research 2010).

  • Women have higher emotional intelligence

I remember a female friend complaining that she had met a great guy… On paper.
But she couldn’t date him anymore after she opened up her heart about a recent painful event… And he immediately moved the conversation toward sports.

How to blame her?
Sure, that guy was exceptional, but women, on average, are markedly more emotionally (and socially) intelligent than men (Smieja et al., 2014).
And that’s a very important trait to define a person’s overall quality.

  • Women care more

If we use conscientiousness as a measure of general “caring”, some psychologists say that women score higher (i.e., Jordan Peterson, author of “12 Rules for Life“)
But the findings are contentious, to say the least (Weisberg et al., 2011).

Where there is little arguing, though, is in personal care.
On average, women take better care of themselves.
From what to wear, to personal grooming and hygiene (Statista, 2016) women take more care of themselves.
And caring about oneself is one of the very basics of personal value.

Where does this all lead us?
Well, it’s funny that when I say this, some women start cheering, as if they had won some competition (facepalm).

But this is a case of the “winner’s curse,” and it reminds me of an old saying: it’s lonely at the top.

woman on mountaintop

5. High-Quality Men Are Under-Supplied

As women have been improving their conditions, men have lagged behind.
And in some areas, there are just too few men in general:

  • More women in urban areas

The gender split in cities varies widely, but a Columbia University paper shows women outnumber men in big cities (and the authors propose they’re there looking for men).

When looking at statistics, we should take into account that gay men show up as male but are not looking for female mates. And there are twice as many gays as lesbians.

  • Whole world regions have more women than men

Some regions of the world also see women outnumbering men.
One little-discussed reason is that transexuals, such as men who feel like women and thus are not available partners, skew the statistics.

In countries like Thailand and the Philippines, the gender ratio penalizes women in very significant ways (and that’s why many Europeans enjoy Thailand).

  • There are far more low-quality men

Finally, men are overrepresented in the (almost) “undatable” lowest rung of society.
Men use drugs at almost double the rate of women and are more likely to:

In some regions of the former USSR, alcoholism has contributed to making those countries terrible markets for women to meet men.

Writes evolutionary psychology researcher David Buss:

This trend is exacerbated by women’s high standards for a mate: their choosiness dramatically shrinks the effective pool of eligible men. This leaves just a few survivors—men of reasonable social status, with adequate self-confidence and good resource potential, who are willing to commit—over whom women then compete.

6. For Many Men, Looks & Youth Trump Success

On average:

Men value most youth and attractiveness (genes) while women include social status, and resources.

That’s a generalization, of course, but research confirms it over and over (Regan et al., 2000 as an example).

And men who have the ‘power’ to go for these women, often do.

The average age difference between heterosexual couples tends to be above 5 years in developing countries and around 2-3 years in developed countries (Zhang, 2007).
But here’s the catch: most men still prefer younger women (OKCupid study).

That wouldn’t be a problem for average women. But since we are talking about successful women who want successful men, well… The rules change drastically for successful men.

They change because many successful men can date younger women. (remember the comparative advantage).
And many of them, do.

These findings are confirmed by data (Pollet et al., 2013).
The richest 400 men in the US married women who were on average 7 years younger. But when they remarried, they chose mates who were on average 22 years younger.

This must not necessarily be a case of “gold-digging” and I find it judgmental at best -most likely manipulative– to label “gold diggers” or “insecure old men” people who choose to date each other.

We could indeed also theorize that there is a strong relationship between resources, genes, and personal character.
The most successful men also showed a lot of grit, determination, and intelligence in amassing their fortunes.
And that makes them attractive fathers, no matter their age.

7. Many Career Women Lose In Femininity

And men prefer feminine women (Little et al., 2014).

This is also part of the general male preference for women who are less dominant, lower status, and less successful than they are.
Quoting from the latest Oxford Handbook of Evolutionary Psychology and Romantic Relationships:

Physical dominance, size, muscularity, and wealth are traditional cues or instantiations of status.
These features are unlikely to help women attract men and may even render women less attractive as prospective mates.
For example, being too tall can harm women’s mating prospects (…) a taller woman (e.g. , 6’4″) must compete with shorter women (6’4″ and below) for the few men taller than herself (6’4″ and up).
Similarly, being too intelligent, educated, or high-earning—other markers of what we typically think of as status—might also be considered potentially harmful to women’s success in mating competition (Bertrand & Kamenica, 2015; Folke & Rickne, 2016)

The downfall of femininity is two-pronged: cultural and professional.

The de-feminization of career women is not entirely women’s fault. In large part, most industries and businesses reward traits that are more associated with masculinity than femininity.

It’s not an accident, indeed, that Elizabeth Holmes decided to lower her voice to increase her authoritativeness and corporate clout:

Elizabeth Holmes: (trying to adopt a lower, more masculine voice)

Of course, correlation is not causation, and many career women might be more masculine to begin with. But still, it’s most likely a mixture, and I wouldn’t discount the nurturing side of it.

8. Successful Women Lack Dating Skills

Many successful women date poorly for a variety of reasons:

  • Mistakenly believe their success makes them great catches

And then get bitter when some men don’t recognize them for the great catches they believe they are.

  • Some career women adopted combative “feminist” social roles

Social roles are OK… Unless they come with baggage.

And self-identifying as “feminist” often comes with a very unattractive dose of bitterness and, in the worst cases, man-hating (yes, extreme feminism is the female version of toxic masculinity).

Just read Lean In, the most popular book for “feminist career women”, and you will easily recognize a combative, bitter undertone.

  • Career women don’t date assertively enough

Most women don’t date assertively enough.

And career women are not the exception.
The (false) belief that their accomplishments make them great catches leads successful women to date too passively.

Mark Gimenin even says that game theory factually predicts that successful women lose out in dating because, feeling like they have a strong hand, they don’t bid aggressively enough.

Then the least successful ladies come in, and they’re ready, available, and fun… And they pair up with the successful men.

  • Believed in the lie that men and women are the same

That lie comes with many harmful consequences for career women’s dating options.

They include the belief that her resources were going to give her dating leverage, that femininity was a thing of the past and that female open ambition came at no cost (and as we’ve seen, they’re all wrong).

9. Smaller Issues Compound

We have already listed the main issues with career women’s dating success.

But to compound the dating woes of successful women:

  • Metrosexuals are on the rise (and male testosterone is on the decline)
  • More libertine cultural trends favor high-quality men (but not women)
  • Successful women are targets of exploitative men, including psychopaths (see “Hare, 1993“)
  • Lower value men may naturally resort to abusive tactics to keep successful women

See here:

Lucio: Men dating higher-status women have less ability to add value, so they must resort to value-taking approaches to keep her

How to Combine Dating & Career Success

So far, this article might have seemed a bit depressing.

But first of all, exceptions always apply.
Plenty of men like successful women, and many successful women have perfect relationships.

Still, here are some tips to maximize your dating success:

#1. Plan Your Dating With Data

If you care about getting married and having children, do consider the gender split of:

  • The city you’re moving to
  • The university you will attend
  • The field you’re working in

Or, at least, take into account the gender split of your:

  • Hobbies, bars, and places you frequent

Sure, art galleries are nice, and wine tastings are sublime (I agree). And maybe you can meet some exotic and romantic Italian or French men. But if most attendees are women, what are the chances?

Be Aware of The Racial Divide

The gender split in education differs heavily among ethnicities.
Asian men are holding up, and there is little difference between men and women (no pun intended on Asians’ lack of hair :).

White men have lost much ground, but worst of all, it’s for Black women and Hispanic women.
Keep that in mind.

successful black women
Black college guys, anyone?

#2. Expand Your Dating Pool to Non-Graduates

Of course, there is a correlation between the level of education and overall quality, but that correlation might not be as strong as you believe.

There are plenty of great men who didn’t graduate

In my own household, my mom went to college, and my father didn’t even finish high school.
But there are some doubts as to who’s the intellectually dominant partner in the relationship (and yes, there is such a thing as intellectual dominance).

IQ and education are also only two aspects of quality. Men can be masculine or high quality in plenty of other ways (i.e., good with repairs, in great shape, good in bed, very caring, etc., etc.).

#3. Get Real(istic): Perfection Doesn’t Exist

Some career women have super high standards, are perfectionists, and are never happy with themselves.

And they carry the same unrealistically high expectations in dating.

But perfection doesn’t exist. People are flawed. We all are.
Consider turning “good but not perfect” into “good is good enough”.

#4. Lock In Young

“Die young, stay pretty”, sang the rebellious goddess Blondie.

But if you want to live and even catch a successful man, you might want to consider pairing up and getting serious earlier in life.

This is important information because, in this day and age, you will find countless resources telling you the opposite.

And guess what?

It’s always women!

Elizabeth McClintock writes on Psychology Today:

Age-old scare tactics (…) to frighten women into early marriage may do substantial harm and little (if any) good.

Don’t fall for that.

Those narratives sound pro-women and supportive, but they are the exact opposite.

Most women advising other women to “wait” are indeed being rather manipulative as they’re trying to:

  • Handicap and mislead the competition with false information
  • Make themselves feel better with the “misery loves company” effect
  • Improve their own lives by lowering the social stigma of unmarried women

I call these forms of manipulation “pro-group feints“, and their only benefit might be to make you feel better. But not to make your date better.

I have no vested interest in telling women to pair up young instead.
As a matter of fact, I really prefer all women to stay single.

But if you want to be in a relationship, then take heed of rational arguments and actual data.

It’s Basic Negotiation

Basic negotiation principles dictate that you get the best outcome in your negotiations when you have the most options (Ury & Fisher, 1981) and the most bargaining power.

And since it’s been proven over and over that female market values peak earlier, locking in earlier yields the best results.

It’s Simple Math, Really

Simple math dictates that a bad dating market will only get worse with time.

Think of the analogy with a game of musical chairs: in the beginning, most people find a mate because the imbalances are spread over a large population.
But it gets more and more difficult as the faster players catch the best mates.
And in the end, when there are two people left and one chair, 50% of the population is left standing.

Again, this is not to say that women must pair up early.
And it’s not to say that older women have no chances, because that wouldn’t be true.

This is to provide you with good information so that you can make informed decisions.

#5. Stop Selling Your Career Success

Look at what this successful lady once wrote me:

text example of career woman mistake

… And notice my “far from impressed” reply

The lady in this example thought I was going to be impressed by her thunderous career start.
I appreciated that she was a professionally accomplished woman. Until she turned it into a selling proposition.

Then I thought it was cheap, and, to be 100% honest… A bit beneath me.
If you are successful, great. But know that it’s not a huge advantage for many men (and that you shouldn’t “sell it”).

Also read:

As long as you don’t oversell your career achievements, there is no need to hide them either (funny skit from “Sex and the City):

Miranda: I’m a lawyer. At a mid-sized firm. Actually, I was recently made partner. I went to Harvward law school

But instead of bragging, which is very male-like, be smart and more feminine with your self-promotion.

#6. Date More Assertively

Not overselling yourself doesn’t mean you shouldn’t date assertively.
Because… You should.

Here is an example for you of a sexually forward, assertive, yet attractive dating style:

effective way of dating successful men

And if you think that’s unfeminine, she was the most exquisitely feminine woman I’ve ever dated.
Also read:

#7. Mix Femininity With Power

It’s not easy to be powerful and feminine at the same time.
But neither is it impossible.

A few examples of powerful and feminine:

Read the full article here:

Plus, of course, this classic here:

#8. Increase Dating Skills

Yes, there is such a thing as mating intelligence.

In simpler terms, it’s “dating psychology”.

Going too deep on effective dating is outside the scope of this article, but here are some resources for you:

Hopefully, you have been too busy to read too much mainstream dating advice.
But if you have, mainstream advice is for average women, and it’s sub-optimal.

#9. Pick A Sperm Donor

Turns out, you truly don’t need a man, indeed.

Not one in your life, at least, and not even if you want family

Instead of looking for a needle in a haystack while wading through endless disappointments, pick a donor from a sperm bank.
Advantages:

  • Safe and clean, since donors are screened for all major infectious diseases
    • Healthier children, since you can rule out several genetic mismatches
  • High quality, since few men even qualify to become donors
  • Fast & easy, with the time it takes for one date, you can browse hundreds of profiles

Of course, these are all on average.

Not all genetic and hereditary diseases can be tested, and IQ is not a screening requirement.
But it’s still safer than any random real-life guy, and you assess the donor’s IQ and life achievements from their profile and interview.

See a donor profile example.

2 thoughts on “Why Successful Women Struggle in Dating (and How to Win)”

  1. I would say also that some career women can see men on a similar level to them in the workplace or even in education as a threat. Even guys they are attracted to they can come to view as the competition and jealousy can arise. Any achievement such a man may make, i.e promotion, a good piece of work, etc can prove counter productive in wooing a career woman. Rivalry can set in possibly in a kind of love/hate mentality particularly for the woman. I have come across this and been party to this several times. Tends to always mean no chance of a relationship and even potentially worse backstabbing tactics from a woman who once saw you as a potential partner. Conceeding or going for a lesser social status job tends not to work either as your then seen as not worthy enough, lol. Only a guy who is way above in social status might meet the needs of such a career woman, perhaps.

    1. That’s a very interesting comment, Phil.

      If she sees you as a threat in the workplace, then yes, you might have a good point.
      If she’s very driven, winning the career race might become more relevant than finding a mate.

      However, in those cases, she doesn’t see him as “above her”.
      She sees him around the same value and, possibly, slightly below -since she believes she deserves a better career and can beat you to it-.
      The moment you show being better than in the workplace, the race will also end and attraction will skyrocket (the movie “Up in The Air” with George Clooney shows this exact dynamic).

      However, that mostly partakes to people in the exact same team, or at least vying for the same position. Being in a different department, even if still within the same company, should remove the competition that stands between (possible) love and romance.

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