Dec. 19, 2025 - Freedomain Radio - Stefan Molyneux
31:37
Why Dating in Your 30s is HELL!
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All right, Stefan Rolling you from Free Domain.
Hope you're doing well.
Hope you're having a lovely, lovely day.
Have a little bit of time before my Wednesday night live this year of our reason, 17th of December 2025.
So here's a question or I suppose a series of observations around dating.
I'm really quite fascinated by sort of the modern dating market.
So trying to understand why it's become so asymmetrical.
Why is it that women have become so picky?
Why is it that men have become quite bitter?
And women have become bitter as well because they can't find suitable partners.
Men can't find suitable partners.
So what I want to do, of course, is I want to go into the backdrop or the backstory of how dating evolved in society.
Dating is kind of a modern thing as a whole, where you just go on a couple of dates.
If you like each other, maybe you become boyfriend, girlfriend.
Maybe this goes on for years.
Maybe you get married and so on.
We're really not designed for any of that, as I'm sure you're aware.
We're not designed to choose our own partners from a kind of void of knowledge, right?
That's not really a thing that we're designed for.
So the way that it worked in your village or your tribe or your farm or whatever, your little community, is that you would know the girl.
You'd grew up with the girl.
You'd know her well.
You'd know her family.
And there wouldn't be much guesstimating.
There wouldn't be much guesswork in who it is you're going to marry.
And this is why there's a particular ring to the phrase, you know, we were high school sweethearts, right?
We were high school sweethearts.
That's considered very plus, very positive and very good.
And that's, of course, the way that it should be, that you should know the person, you should know their family, and you should not be picking blind.
And also, your parents should have the kind of successful marriage that gives them great credibility when it comes to choosing your partner.
Because you want to find a sweet spot between lust and moral appreciation.
Or let's just say, because it's hard to say the people in sort of human history were super moral, but let's just say value compatibility.
So for men, there is the challenge between a woman who's just smoking hot and a woman with whom they share values.
I remember there was a girl in my high school.
She played cello.
She used to wear this t-shirt that said cello power.
Not particularly attractive at all, like a four, but very good natured, very sweet.
We used to chat a lot and would have been a great partner and girlfriend and wife and so on.
But some value compatibility.
She was very intelligent for sure.
And yet it would not really have crossed my mind to ask her out because I was unfortunately in the untutored shallow phase of my life.
Now, why does physical attractiveness matter?
Well, because physical attractiveness is a proxy for good health.
Even features are a sign of good genetics.
Lustrous hair is a sign of good health.
A good hip to waist ratio is a sign of fertility.
And so good looks are a sign of good health.
And so good-looking children are more likely to succeed because, you know, we want to have kids who themselves are going to have kids.
If you knew ahead of time that your children would never have children, would you bother to have children?
I mean, almost certainly not, right?
You take your money and do that coffee tour of palazzos or something like that, right?
So, so we want to have kids who themselves are going to have kids.
And physical attractiveness is an important part of being able to have kids, right?
Somebody who's really funny looking is less likely to reproduce than somebody who's very good looking.
So looks are a proxy for health, and looks are a proxy for economic success.
So looks matter.
Looks matter.
If they didn't, they wouldn't, right?
Or to put it another way, evolutionary preferences and pressures for good looks exist for a reason.
So all these people who say, well, you shouldn't just choose on looks.
Well, sure, yeah, but looks matter.
Looks matter.
If you marry some very ugly man, right, as a woman, and you know, some very short, ugly man, then your children are more likely to be, let's look at the male, short and ugly.
And do short and ugly men generally do well in the daily market?
Well, in the past, somewhat.
In the present, less so.
Because social media dating apps, living in cities have all given women the illusion of an infinity of choices.
You know, when I was a kid, believe it or not, I'm not talking about horse-grown drawn carriages, but when I was a kid, there was public transport buses, right?
And when I was a kid, sometimes the buses would cluster, right?
So you'd see three buses coming along at the same time.
And if the first bus was like really full, like jammed to the rafters, then you'd say, you know, you'd wave it off.
I'll take the next bus, right?
I'll take the next one.
And that's what you do.
Now, if it was the third bus and it was still really full, then you would just take that bus and wedge your way in, right?
Unless you saw a fourth bus coming along, right?
Assuming they're all going to the same place, right?
So if there's another one coming along, then you can wait for optimum circumstances.
If you're trying to sell your house for half a million dollars and you get an offer for $450, but the real estate agent says, I've got five other offers coming in, you're not going to take the $450 because you're going to wait for the other office coming in.
To go back to the bus analogy, of course, if it was the last bus of the night, right?
So the buses are used to be, I want to have to get back from downtown, and the last bus would run at like 1, 1:30 in the morning.
And so if it's the last bus, you're going to jam your way on because otherwise you're going to have like a two-hour walk, especially if it's winter.
That is a pretty unpleasant stroll, to put it mildly.
And if you got to mash your groin into somebody else's hip for half an hour, you'll find a way to do it, right?
Because it's your last bus.
So of course, if you think that there's an infinity of buses coming along and the ride is going to be for the rest of your life, then you're going to wait, wait, wait.
And then what happens is the buses run out because you get too old to date in that kind of way.
So in the past, when everyone got married off by, say, 20 or 21, you had to choose the best guy you could get with the knowledge that you couldn't keep choosing forever.
It's sort of like, you know, that game, musical chairs, right?
There's a bunch of chairs.
And there's music.
And when the music stops, like there's one less chair than the people, you get 10 people, nine chairs, and you just grab the closest chair because you don't want to get out of the game.
You don't want to be kicked out of the game by not having a chair, right?
You'll even pull chairs away from other people, which is like stealing somebody else's boyfriend or girlfriend.
So there's a countdown.
The good people are being taken and chosen.
And if you're a five, let's say you're a woman who's a five, and you want to choose a guy who's a seven, maybe you'll get him, but the seven is looking for an eight or a nine.
So if you choose it, you aim at a seven, but then the seven gets taken by an eight or a nine, then you've got to maybe switch to a six, but maybe the six has been taken, then you switch to a five.
Oh, the five got taken by a six or another five, and then you, right?
So if you aim too high, you end up with less.
And that's a sort of foundational calculation for women, right?
Which is like if you don't find any bus to your satisfaction, then maybe, just maybe, this is after a while, the last bus comes by and they just get, then you just have to walk and then you're kind of messed, messed up, right?
So men and women have to choose, had to choose each other young.
So what does that mean?
Well, if you look at a young woman versus a young man, there is, of course, an asymmetry in that she is at maximum fertility, right?
Say an 18-year-old man, 18-year-old woman.
Some places you can get married younger, but let's just go with sort of legal adulthood.
So you're an 18-year-old male.
I'm going to call them a boy and a girl because they're just out of childhood, right?
So you've got 18-year-old boy, 18-year-old girl.
The 18-year-old girl is at maximum fertility.
She's got, you know, 20 years of fertility ahead of her.
Her eggs are fresh.
Her energy is high.
Her sexual attractiveness is high, and so on, right?
So she is at her maximum value.
The man, the boy, the 18-year-old boy, is at his minimum value, minimum value.
Because a woman is at her maximum fertility.
A man is at his lowest income potential.
She's never going to be more fertile.
He's never going to be more broke than at 18, right?
So the man and the woman, the boy and the girl, they have to get together when things are wildly asymmetrical.
And he has vastly more knowledge than she does.
Now, of course, that's true that some women are infertile and so on, but that's very much the exception and so on, right?
So he has knowledge, certain knowledge, that she is at her maximum fertility because she's 18.
So he knows that her value is the highest.
However, she does know, she does not know what his value is going to be over time.
Is he going to make a lot of money?
Is he going to be a good hunter?
Is he going to be a steady provider?
Is he going to be reliable?
Is he going to cheat?
Blah, blah, blah.
Now, she could cheat as well, but it's a little less likely for her to cheat when she's got five kids under the age of six crawling all over her, right?
So he chooses with maximum knowledge, and she takes maximum risk.
If she chooses wrong, if she chooses a guy who turns out to be lazy, if she chooses a guy who turns out to be dumb, if she chooses a guy who turns out to be a drunk, or just, even if he's hardworking, just incompetent.
You know, his vision goes squiggly at the age of 25 and he can't hunt or he can't farm or whatever, right?
Or he's a show-off, so he does things beyond his physical capacity and gets injured, like hurts his back, or something terrible, right?
Something really catastrophic for his productivity towards their children.
So her maximum value is in the present, but his maximum value is in the future.
See that it's your challenge: bird in the hand, two in the bush.
Her value is maximum and evident.
His value is future and potential, which is why men propose.
Because she has to know that he's organized enough and decisive enough and courageous enough and sort of you name it to pursue her, to woo her, to bring her flowers, to propose, to write her poetry, to whatever he's going to do, right?
She has to know that he has at least the assertiveness, if not the downright aggression, to be decisive and to ask her out and to not wait and wait and wait or defer or just hang around without actually asking her out.
Because if he's afraid of rejection, he can't win in life.
Because to win in life means to be rejected all the time.
And if he can't handle rejection, then he's too insecure to go out and compete and get resources.
So that's how we evolve.
That the woman has to be skeptical.
And what is the woman looking for?
The man is looking for signs of fertility.
The woman is looking for signs of intelligence.
At least in colder climates in particular, because you have to have a man who's going to plan for and get through winter.
So the woman is looking for signs of intelligence, which is why, well, intelligence, martial courage, a woman is looking for the ability to defer gratification and courage in the moment.
A reasonable amount of courage, not an excess which is foolhardiness or a deficiency, which is cowardice.
So a man who is short and homely and from a bad family, who then approaches a rock-solid nine or ten, well, he has an excess of courage and does not judge situations well.
Because he doesn't judge situations well, he's going to fail when it comes to cooperating or being an employee or working with other hunters or getting everyone together to raise a barn because he's too vain.
He's too arrogant.
He doesn't understand his own place in the pecking order.
And certainly, if you've been to junior higher high school in government schools, maybe private schools too, everybody knows that there are these people who are really vain.
They think they're all that and they're wrong.
At the same time, if a guy is very shy and very awkward and so on, then it may arouse her mothering instincts, but not her mating instincts, and he is going to be too deferential to win in a brutal competition.
Basically, all men are judged by women to some degree according to the fantasy of combat.
Your woman looks at you and imagines you in a fight.
And if all she can do is picture you losing that fight, crying and blubbering on the ground with your nose broken, then it's going to be a little bit hard for her.
I mean, that's just natural, right?
There's nothing wrong with this.
It's just how we evolved.
Because violence was a pretty common way for men to settle their disputes.
And she did not want to get involved with a guy who would get beaten up and have his stuff taken away from him.
So let's fast forward to 35.
Let's say that the man and the woman are single at 35.
What's the difference?
Well, the difference is enormous.
So now the woman, from a reproductive standpoint, is at her lowest value.
And I'm not kidding about this.
You say, ah, yes, but she's still more fertile than she would be at 80.
And it's like, well, yeah, but no man will date a woman of 80 with the hopes of having children, but he'll date a woman of 35 with the hopes of having children.
So she is at her lowest value from a reproductive standpoint because it's possible, but less likely, right?
And it's not uncertain.
It's certain.
He doesn't know how infertile she is.
Of course, down to the last detail, nobody does.
But he knows that well over 90% of her eggs are already gone.
So she is at her lowest level as far as fertility value, sexual market value goes.
And a woman of 18 can be beautiful without skepticism.
We're not skeptical of that, right?
However, if a woman of 35 is physically very attractive, then the man has the question of why is she still single?
If she's very attractive, why is she still single?
And that is a very good question that kind of needs to be answered, right?
So she is at her lowest sexual market value.
Again, I just want to reiterate, if she's 50, you say, oh, no, but she's even lower.
It's like, no, because at 50, no man is going to try and have kids with her, right?
But at 35, you could try.
So she's at her lowest family marriage market value.
Now he is at his highest sexual market value because it is no longer a matter of guesswork as to how successful he's going to be because he's had already 20 years in the workforce.
You know, most people get a job mid-teens, or at least they used to.
So his value is now proven.
I mean, what's the old saying, if a man has seen, any man seen riding a bus after the age of 30 has been a failure in life?
It's a little true.
So she doesn't have to guess.
A boy of 18, you have to cross your fingers and hope he's going to be successful.
By the time he's 35 and has been in the workforce for 20 years, you know.
You know, goes to school at 17 or 18, graduates in his early 20s.
By 35, he's had 12, 13 years out there putting the rubber to the road, so to speak.
So all of that is known.
She doesn't have to guess.
So the problem is she at 18, highest sexual market value.
He at 18, very attractive, obviously, young men of 18 and young women of 18, sort of at the peak of physicality.
But in terms of the business of having and raising babies, she's maximum, he's minimum.
And that's kind of what we've evolved to process.
A woman who tries to settle down at 35 and wants another 35-year-old man, he is maximum, she is minimum.
Now you say, oh, but he's not maximum because a man's peak earning power tends to be 40 to 50 or so.
So he's not peak.
It's like, well, he kind of is, though, because a lot of women don't want to start children with a man who's 50 or 45 because he's getting too old.
Especially if it's his first marriage, then he's, you know, reached sexual maturity in his teens.
He's now in his mid-40s or he's 50.
I mean, that's a long time, right?
That's 30 plus years of non-experience with long-term commitment and compromises in relationships.
So he is peak because he's young enough that he's still aspry and handsome-ish.
He's got his earning potential is now proven.
And he's still young enough that you can have kids and he's still got 40 years to go.
So the kids are going to be long-grown.
There'll still be time to invest in grandchildren and so on, right?
So he's peak.
A 35-year-old man is a rock star.
Now, the problem, of course, is that she has not experienced her decline, but he has experienced his ascension.
So I'll tell you what I mean by that.
This is one of the reasons why dating in the 30s is so tough.
So he has experienced going from broke to relatively well-off.
So he knows the difference.
I very, by the by, I very, very clearly remember when I got my first office job and was starting to make some good coin.
I very clearly remember how good it felt to actually have some sort of stable income that came from a job with some stability and some growth opportunities and so on, right?
That wasn't like waitering or something.
So he's gone from making 10, 15 bucks an hour intermittently to making like 40 bucks an hour.
He's gone from not having a car to having a car.
He's gone from not having a place to having a place.
He's gone from having no savings to having savings.
So he has from 15 to 35 really felt his ascension.
And at 35, you know, assuming you're reasonably active, you don't have a big issue with like aging or anything like that, right?
So he has very vividly felt his ascension.
She, on the other hand, has not really felt her decline because, I mean, I don't know, women get crazy upset when you talk about egg decline and so on for reasons that make sense, right?
But she's not really experienced her decline because she's still reasonably attractive and she also always has the option to subsidize relationships with sexual access.
So she can still get guys, she can still get men to sleep with her, she can still get men to date her for months or maybe a year or two or whatever.
So she has not experienced her decline because women keep score by relationships and being attracted to not by the only thing that really matters, which is a man in public on his knees with a ring making the proposal.
She's still able to pull guys.
She's still able to date.
She's still getting her inboxes flooded and blah, blah, blah.
So she has not experienced a decline because she is measuring male interest in her, not male commitment to her.
And she might have been able to, let's say she's a seven, she might have been able to get an eight to commit to her when she was young, but she can't now.
And she's kind of bewildered, which is like, well, these guys all want to date me, but they won't commit, right?
It's incredibly frustrating.
Honestly, for men, it's like, and men have certainly experienced this, right?
But for men, it's something like this.
It's like, I keep getting these job interviews and I keep getting called back for these job interviews.
And they go on for weeks.
And I write these tests and I get interviewed by more and more people.
And this has been going on for years, but I never get a job offer.
Or if I do get a job offer, it's pulled.
Like, I just can't get a job.
Maybe I can get some temp work or something like that.
I just can't get a job.
I can't get hired.
I can only get interviews, which is like dates or dating or whatever they go on, but the man won't commit.
So it's incredibly frustrating.
And then what happens is because the woman is her standards get higher as her value goes down, which is really tough.
You know, if you know a computer language and that computer language is being phased out and you say you want double your salary for a mostly obsolete language, it's going to be pretty tough, right?
If you've been fired from a whole bunch of jobs and then you double your salary requirements, that's going to be pretty tough for people to accommodate, right?
Because they'll be like, well, hang on, you got fired from your last five jobs.
Why do you want double the salary?
Right.
So as your value goes down and your demands go up, there's a market mismatch.
It's really foundational.
So she has not experienced her decline because she judges her value by dating, attraction, and sex, not by proposals.
She feels more valuable because she has more experience, she has more money, she has more prestige, she got educated, she has dating experience, she's more confident, she's what?
So she feels that her value has gone up.
But instinctually, a man judges a woman by future children.
Can you give me three to five kids?
I mean, that's what we're programmed for.
You may disagree intellectually, but you may only want two kids or no kids, but that's what we're programmed for.
That's what survived.
Because half of the children died before the age of five.
So replacement birth rates were five to six kids.
And we have an instinct for these kinds of things.
You know, one of the sort of theories that I have is that one of the reasons why men are very good at making women laugh is you can try and figure out what their laugh lines are like, how old they are.
So the male is at his maximum value and the woman is at her lowest value.
And that's almost, of course, a complete mirror image of 18.
18, woman maximum value, man minimum value.
At 35, man maximum value, woman minimum value.
And she doesn't know it.
He knows it.
And this is why there's this sort of desperate battle from women in their 30s to call men who want to date younger creepy.
Oh, she's too inexperienced.
It's high pedophilic, you know, that kind of stuff, right?
But that's just standard female competition stuff.
It's not to be taken with any seriousness.
I mean, they don't do that to refer to Cher or Madonna or these Botox ghouls preying on younger men.
So the woman then, how does she try to win a man?
Well, a man who's successful in his 30s and single has fought hard to be successful.
He's been involved and engaged in long battles, long.
So what's he looking for at home?
He's looking for peace.
He's looking for peace.
And he's looking for submission.
Now, I'm aware that's blah, blah, blah.
It's a volatile term.
I don't mean a woman who just nods and smiles at everything that he says and doesn't have any opinions of her own because that's about as interesting as watching paint dry.
But what I mean is that he's looking for somebody who's not punchy, fighty, challenging, high stress, neurotic, high maintenance, you know, paranoid, desperate, suspicious.
Like he's just looking for peace because he's already out there fighting.
You know, after the boxing match, he wants a massage, not another boxing match, right?
Whereas the woman, if she's a career woman, she has, you know, been fighty and aggressive and, you know, whatever.
And that's fine in the business world, but it just doesn't, it's not that appealing to a man who is successful because successful men have combat at work and want peace at home.
Otherwise, you just burn out.
And I remember in my early 30s, I remember dating women in their 30s and being baffled by their confidence and expectations.
And I didn't understand it really at the time.
Just baffled by their confidence, their demanding stuff, their expectations, and so on.
And it's like, but what?
Like, I'm a high-value man and you are being difficult in this kind of way.
Like, I don't, I mean, I wasn't being difficult, but I was just like, you're being demanding?
Like, what?
And again, because I've been a hiring manager, people could be demanding, right?
I mean, you can get the brown M ⁇ Ms taken out of your M ⁇ M bowl in the dressing room, but you better be Van Halen.
You better be able to fill a stadium, right?
So it's a real mismatch.
And it's very tough for an attractive woman in her 30s who's been the object of male attention for 20 years and has had a lot of deference because of her youth, high value, fertility, and attractiveness, to swap that around is very tough.
I mean, I would say functionally, it's really impossible.
And this is why it's so tough to date in your 30s.
For a woman to say, I am now low value and must work to woo a man and win him over when she's been used to 20 plus years.
It's like asking the king to become the servant.
It's really tough.
I mean, I had a friend who was in his 30s.
He was dating a woman in her late 30s, and she was kind of bossy and kind of demanding and kind of imperious and so on.
And he's like, I don't get it.
Like, I'm her last chance for family and she's being difficult.
And again, I didn't really understand it at the time.
It didn't, I kind of kind of, I got it instinctively, but I didn't.
And I wrote a novel in part about this, but about a woman who, I wrote this almost 30 years ago, it's a woman who has to check off, like sort of cross off things on the list because she was in her 30s of what she wanted in a boyfriend, that she was willing to humble herself.
And she made that transition, but very few women do.
And it's a basic depopulation strategy is to pump up women's vanity by having them equate sex and male attraction with sexual market value, which it's not.
I mean, that's like a guy who buys women $5,000 necklaces to go on dates with him, thinking that he's really attractive and that they really want to marry him for him.
It's like, no, you're subsidizing it with a lot of money.
And for women to subsidize their relationships with sexual access is not an honest gauge of how attractive they are and what they can actually pull or what they can actually achieve.
It's like if you're working at daddy's company, it doesn't tell you much about what you're worth on the open market.
So, yeah, if you've said, well, I've only had one job, I worked there for a year and my father was my boss and he hired me, then it'll be like, well, you know, you know, it seems like a bit of nepotism.
And it would not be any competent manager would not say that that's a great gauge or judge of your abilities.
So I hope that makes sense.
And if you have, of course, different experiences, always love to hear them.
Please do let me know.
And if you could support the show, I'd really appreciate that.