Why Successful Women Fail At Dating (& How to Fix It)

single successful woman

Successful women are not nearly as successful at dating.

Most of us have heard or experienced anecdotal evidence of successful women’s dating woes.
You know Jane, that smart, accomplished, high-income career woman… Who’s just so poor at dating and can’t manage to find and hold onto a good man?

Well, as it turns out, there are millions of successful Janes.
And it’s not just anecdotal; studies show that high-status women are less likely to have mating and reproductive success.

But why’s that?

This article will tell you why successful women fail at dating. And it will then provide you with the solutions.

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 an easier time meeting attractive dating options than successful women do.

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 own 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).

Submissive Women VS Strong Women: Who Wins at Dating?

  • 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.

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.

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 a subjective term, 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.


  • 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 Trump Success

Women are into hot women, we know that.

But here’s the interesting bit.
We made the point that men prefer women who are less accomplished than they are.
And yet, most couples still often match each other in terms of overall value.

How come?

It’s because what the two genders seek and exchange in the sexual marketplace is not exactly the same (in international trade, it’s called “comparative advantage“)

That means that transactions (i.e., marriages) can happen with wild imbalances of specific traits.
Take attractiveness, for example: an ugly man can marry an attractive woman because he has resources.

On average:

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

That’s a very high-level generalization, of course, but it’s been confirmed by research over and over again (Regan et al., 2000 as an example).

Since attractiveness is not highly correlated with life achievements, it’s often relatively easy for older but successful men to end up with unaccomplished but attractive women.

In case you’re wondering, trade-offs are consistent with evolutionary psychology theories and well documented in the literature (see Stanik, 2009).

7. For Many Men, Youth Trumps Experience

This is a contentious one.

But we don’t let contention stop us on our way to the truth.

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).

Many older men don’t date younger women because they can’t, not because they don’t want to (exceptions apply, of course).

And 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.

If you don’t believe the data, you can listen to hyper-realist Samantha from Sex and The City:

However, please maintain a judgmental attitude.
This must not necessarily be a case of “gold-digging” and I find it aggressively offensive to label “gold diggers” or “insecure old men” as men or women 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.

Note: there are exceptions
Some successful older men do prefer women closer to their age.
Evolutionary psychologist Geoffrey Miller says that life experience and maturity make for emotionally more fulfilling relationships, and some men appreciate that (Miller, 2000).
But usually, you’re better off working with the rule, rather than seeking the exception.

8. Career Women Are Not Feminine

… And men prefer feminine women

This one will not go down well with some female readers.

But, again, it’s either rejection of reality and fantasy or reality.
And both common sense and studies prove that men prefer feminine women (Little et al., 2014).

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:

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.

9. Successful Women Date Poorly

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).

10. A Host of 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)
  • Our culture of easy sex favors high-quality men (but not women)
  • Anti-harassment laws made some men overly scared of office-dating
  • As some rich men are targets of gold-diggers, career women are targets of psychopaths (see “Hare, 1993“)

Career Women VS Successful Women

Some authors have complained that the expression “career woman” is sexist because we don’t use the equivalent “career man”.

I don’t enter into the discussion, but I use the term “career woman” because it defines a specific class of successful women.
I define a career woman as:

A career woman is a woman who earns or is planning to earn an above-average income, does well or extremely well in her profession, takes her job seriously and prioritizes her career over many other aspects of her life

That is a very different definition from a “successful woman”, who might be successful in a myriad of ways and possibly not even work at all.

And it’s also very different from the more general “high-quality woman“.
A career woman is not necessarily a high-quality woman, and a high-quality woman does not need a career or job to be high-quality.

High-Quality Women Have Better Dating Options

The distinction is also important for our analysis because a career woman presents a very different sexual market value than a high-quality woman who’s not pursuing a career.

It’s indeed much easier for a high-quality woman who’s not busy climbing the corporate ladder to be feminine and charming.
Most high-quality men will take a more feminine woman with little or no income over an unfeminine one with a high income.

Thus, a high-quality but non-career woman has much better dating options (also read: archetypes of alpha females).

Alpha Female: 10 Types of Leading Women

Limitations of this analysis

This is a general analysis of the sexual marketplace for career women and successful men.
And as with every general analysis, it does not apply to every single market player.

To begin with, the variance in personal preferences in dating and relationships is notoriously high (Wiederman & Dubois, 1998).

Even attractiveness markers, which tend to be more stable for men, present plenty of exceptions (we all know that guy who’s into older women or who places high importance on intelligence).

For more on exceptions, see:


Another variable we haven’t taken into account is the type of relationship between the man VS the player, with the former placing more importance on internal qualities such as personality and intelligence (also see: the psychology of womanizers and lovers VS providers).

And of course, this article is written from the point of view of a career woman who wants a relationship.
But of course, it might be the case that a woman is not interested in a relationship (or in a relationship with a man).

However, the overall analysis holds true because exceptions are exceptions, and you don’t make the rules with the exceptions.

What’s The Solution?

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

But in my opinion, it’s never depressing to know the truth.
The truth will set you free.

And once you know the truth, you can get down to realistic solutions that work.

So let’s talk solutions now.

#1. Know Your Stats

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: 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):

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:

Feminine AND Powerful: 9 Tips For Women Bosses

Plus, of course, this classic here:

#8. Increase Your Mating Intelligence

Yes, there is such a thing as mating intelligence.

In more simple terms, it’s basically the equivalent of “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.
Instead, go for the best: Seduction University.


This should be superfluous, but I want to make it abundantly clear that this article is not a denigratory piece towards career women.

This is not an invitation for women to work less hard or drop their careers—quite the opposite: I prefer financially independent women, so keep on rocking, lady!-.
And it’s not even an invitation for men to “step up,” -albeit that wouldn’t hurt them-.

This article showed you that, factually, there are some roadblocks for career women toward a happy and fulfilling relationship.
However, it also showed you that there are solutions.

This article shows you a path.
Whether you are going to walk it—or whether you even want to walk it—is wholly up to you.

2 thoughts on “Why Successful Women Fail At Dating (& How to Fix It)”

  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. Lucio Buffalmano

      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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