An Open Letter to a Smart Young Man About Dating Women

0.

Dear [redacted],

It’s been a while since we spoke. You’re finishing high school and starting college soon, no? Very good. One of your parents (I won’t say which) asked me to talk to you about dating issues. It’s not that they couldn’t tell you some of this stuff themselves. It’s just that teenagers often don’t want to listen to things coming from their parents.

From your point of view, this is basically unsolicited advice. The first rule of interpreting unsolicited advice is that it is nearly always actually about the person dispensing the advice, and only somewhat about the person to whom advice is being given. Solicited advice is fundamentally different in this regard. Usually, the most heartfelt, passionate advice that people give is addressed to a younger version of themselves, no matter who the nominal audience is. It is usually about the mistakes they made that they now understand better, but also sometimes about great triumphs they had which their younger self wouldn’t have envisaged. These two possibilities complicate matters. It's somewhat like Freud. He was wrong on the specific point that everyone secretly wanted to have sex with their parents, but right on the broader point that if you want to understand someone's personality, you need to start with the relationship they have with their parents. So it is here. It doesn't mean that unsolicited advice is wrong, it just means you should consider the extent to which you actually fit the same case as the younger version of them, and adjust accordingly. I’ve tried to tailor this as much as possible to a) the parts I think you might actually listen to, and b) the things you might not figure out on your own. It as much about you as possible, subject to the caveats above.

1. 

This is not primarily advice about how women work, or how to find one to date. For that, read the Chateau Heartiste archives, especially the early stuff. You can learn a lot from Heartiste, but you need to be careful. He is at his best talking about applied evolutionary psychology. Follow what Heartiste says, and you will get laid. For a man of your age, this is almost certainly your main concern. But make sure you keep an eye on the positive - how the world works - versus the normative - how ought you act in your life with this knowledge? This is distinct. Just because you can do something doesn't mean you ought to. And we're back at the point above – Heartiste’s advice, like everyone’s, is probably going to be slanted towards being somewhat self-serving. There's a normative suggestion that endless philandering is something that you should do, that it's a life well lived. Well, that's the rub, isn't it? Do you want to end up like Heartiste, at least as much as you can estimate what his life is like?

But you're busy. You don't want to spend weeks reading old blog posts (though you should, they're very entertaining too). Okay, fine. Let me give you the condensed Cliff notes version, as much as I understand it.

Lesson #1.

On average, women will be attracted to behaviors and traits that would have been associated with the alpha male chimp in pre-historic society.

Being big and strong, obviously. But more importantly, how you carry yourself. Are you confident? This is nearly universally stated by women as being attractive. Being confident in a chimp society, if you weren't the top chimp, was a fast way to get yourself killed. Now it isn't, of course, but our brains are still wired the same way. Similar things apply for status and social proof. Acting like you have options with women, and could take it or leave it with any particular girl, is paradoxically more likely to succeed than acting very eager and desperate. Girls can smell desperation at a thousand miles. If you are desperate, it’s all the more important to act like you’re not.

You're a smart young man, and like most smart young men, your social status will probably go up as you leave high school, not down. The dumb jocks peak at age 14. But in the interim, you'd be amazed just how far "fake it" can take you as advice. If you pretend to be confident, it works almost the same as the real thing. Easier said than done, of course, but that's life.

Lesson #2.

In any battle between women's stated preference and their revealed preference, bet on their revealed preference.

Applying this takes some skill, because you have to pay attention to what women's revealed preference actually is, and society tends to give you bad advice on this front. Moreover, you will be tempted to make the worst common mistake that many young men make - if in doubt, they substitute the question "what would I want in this situation", which is generally a very poor strategy. The traits and behaviors that you would want in a woman are generally not the same traits and behaviors that a woman wants in you.

For instance, suppose a woman says that she wants a sweet, funny guy who buys her roses and cuddles her at night. She's not lying, she does want this. But what it's important to realize is that when she says this, she's imagining Brad Pitt doing these things. When a man is high in status, displays of commitment are desired, because the primary worry is that he's going to leave. You, however, have the preliminary problem - how to I become more of a facsimile of Brad Pitt? Not a movie star necessarily, but how do I carry myself like Tyler Durden in Fight Club? This is the problem you need to solve, but women won't tell you this. If you start out being Bob from Accounting and act like their stated preference claims, you'll get fired. If they say they want sweet guys and instead keep going out with the @**hole bass player from the band, you'd do far better learning how to play bass and give less of a damn when dealing with women.

A crude but effective approximation of “bet on revealed preference” is just “act as much as possible like the guys who are successful with women”.

Lesson #3.

Don't be pathetic.

The reason I like this version is that it condenses many things down into one idea, because we all kind of know what "pathetic" looks like. Like many things in life, game advice eventually hits diminishing returns. And the biggest benefits actually come early on, from cutting out the left tail of pathetic, cringeworthy behavior. If you do nothing else, read Heartiste's hilarious "Beta of the Month" series. This will give you a range of examples of terrible behavior to avoid. If you just avoid this kind of thing, you'll be way ahead of the curve.

As they used to say when people still wrote blogs, go read the whole thing. There are only a few blogs I've gone back and read from start to finish. Heartiste is one, and Moldbug is the other.

2. 

At some point, I decided that I was only going to write blog posts about things that I hadn't actually read elsewhere. So think of this letter as an addendum to the kinds of things I've seen written in game blogs, and a way of avoiding the pitfalls that might come from taking 2010-2018 manosphere advice too literally.

Chief among these is the following. One of the most consistently unpopular messages in human society is the reality of the budget constraint. Telling people that life has hard, unpleasant binding tradeoffs, and that something inevitably has to be sacrificed, is a truth that it is human nature to resist as far as possible.

It is extraordinarily unlikely that you will get everything you want. If you are lucky, you will get some or most of what you want, depending on how expansive are your wants. The right choice, in a big picture sense, will very likely involve giving up something else you want, with all the attendant regret that entails.

The fact that people generally don’t want to hear this message goes doubly so for those who write about self-improvement. They’re right to do so for the purpose they have. For game in particular, imbuing a sense of irrational self-confidence is very important when approaching women, especially among self-doubting beginners. It’s not for nothing that I began by saying “read Heartiste first”.

Being irrationally overconfident when it comes to women is great tactics, but not great strategy. In other words, when approaching any one woman at a bar, you absolutely want to be irrationally overconfident. But it doesn’t follow that you also want to be irrationally overconfident about your long-term budget constraint, and what tradeoffs it implies.

The rest of this post is primarily about what some of those budget constraints are, as I see them, and what you should do about them.

3.

Game authors are very good at skewering women's self-deceits and delusions. The largest among these is that they can just date around, prioritise their job and travel, and start thinking about trying to find a husband in their late twenties or early thirties. This is, of course, a disastrous strategy, on average, and comes with a high probability of ending up as a cat lady, or ending up with no children/fewer children than you’d like, if you do find a husband.

But still, there's an equivalent male delusion, and it goes like this.

“Men just keep getting better and better over time.”

It is indeed true that men don't have nearly as steep a decline in sexual market value over time. This is complicated by the fact that wealth and status take on different trajectories, and women's preferences aren't as strictly driven by looks and youth as men's are.

But the basic idea that men just keep getting better seems ludicrous to me, particularly because it violates revealed preference arguments. Limiting oneself to women above the age of consent (here assumed 18), at what age are women the most physically attractive? Probably ages 18-22. Men mostly, but not entirely, have preferences based on age and physical attractiveness, both of which are correlated on average. Great. So who are the 18 year old women actually dating?

The answer is, largely men ages 18-25. The 22 year olds are generally dating men ages 22-28. At least in my observational experience.

Now, part of this is just the mechanics of dating. Who are you actually interacting with? If you're at college, probably other people at college. In a different world, say southern Europe 300 years ago, it may have been much more normal for a 15 year old to marry a 40 year old. But we ain’t in that world. The Smashing Pumpkins put it quite memorably: Love – it’s who you know. At a bare minimum, people the same age have a much higher chance in our largely age-stratified society to meet and interact with hot young women in an environment where dating is on the cards.

But even so, let's consider the hypothesis that 18 year olds are actually more attracted to 35 or 40 year old men. In such a case, we have to posit a fairly significant market failure as to why they aren't dating them. Does Tinder not exist for such women? Could they not just go online and select their desired age range as 35-45? Of course they could. Doesn't revealed preference seem more believable? In this view, your ability to attract 18 year olds probably maxes out at about 22, at least if you’re still in college then. Your ability to date 22 year olds probably maxes out at 26-27. If you're getting better on other dimensions (richer, higher status job), you can compensate partially, but probably only partially.

If you want to date 27 year olds, you'll have a good many years ahead in which you can do this easily. If you want to date college freshmen, you won't. You can still do it, it just involves getting luckier, or drawing from more idiosyncratic bits of the distribution (i.e. paying a cost on some other dimension).

Positing that George Clooney has gotten more attractive to women as he aged is every bit as absurd as saying that Christie Brinkley still looked hot at 50. Neither is remotely representative of the average person's experience. If you want to find out how easy it is for a 40 year old to date 18 year olds, ask a 40 year old. They'll tell you. Or if you don’t believe me, just set up a tinder account yourself with some pictures of decently attractive 40 year old men, set your age as 40, start swiping, and see how many matches with 18 year olds you get.

There is one offsetting aspect to this, however, which is especially apt to confuse some people. Many of the people writing game advice are generally smarter than average. And in my anecdotal experience, smart men who think explicitly about game do so because a) it’s not something that came naturally to them as a teenager, and b) it’s something they only got better at with age. So for these people, the age decline tends to be muted by the fact that their experience with how to interact with women was getting better, at least for some time.

This can indeed offset a good amount of the decline, and as a point estimate will probably actually improve your chances.

But this is best understood as you moving up the cross-sectional distribution over time. It doesn’t change what the age-related decline is for the distribution as a whole.

4.

Why does this matter? Well, in the short term, it tells you that the regret avoidance strategy when you’re just casually dating is to date as young as you can, for as long as you can. There’ll be a good number more years where you can date 25 year olds, but the 18 year olds are going away faster than you think.

But this is a relatively shallow lesson. There’s a more important one.

Suppose you believe, as survey evidence tends to indicate, that marital unhappiness and a woman’s divorce risk increases with her lifetime number of sexual partners. Or, suppose you’re one of the mass of normal men that feels somewhere between uncomfortable, grossed out, or angrily jealous when they think about the idea of one’s dearly beloved having boned other men, especially lots of other men.

Partner counts are a ratchet. They go up, but they never come down.

For any given sex drive that a woman has, her partner count is lower when she is younger.

Add this to the point above, and you have the following.

Your ability to wind up with a wife where you got to enjoy all of her best years and experiences peaks relatively early.

The price you pay is likely giving her most of your best years.

If you choose to spend those years just casually hooking up with random women who you aren’t going to marry, you will get the fun of banging lots of women. But it will probably come at the cost that your wife, when you meet her, will be older, and will have banged more guys already. To make things worse, the longer it takes you to realise this, the more you’ll keep chasing after the dwindling chances of getting the kind of wife you could have gotten if you’d met her at age 22. The longer you wait, the larger the gap between what you ideally want, and what you’re likely to get. At a certain point, you might not end up with anything at all that meets your estimates of minimum acceptable partner.

This is not fun to contemplate, but I think it’s true nonetheless.

I don’t mean this rhetorically to imply one course of action or the other. A budget constraint is not advice. The guys that met their wife when they were both freshmen in college nearly always have regrets about the fact that they didn’t get to have as many years in college and in their 20s being free and single. This message is true, and it tends to get emphasized fairly loudly in the modern world. Which is why I bring up the flip side. The guys that did get to enjoy lots of years of partying in college and their 20s don’t generally get to marry women they met when such women were 18 year old virgins, and go into a relationship with their eventual wife when neither one has very much baggage from past relationships. This doesn’t get talked about at all, because it cuts against much of the grain of modernity to acknowledge that lots of men prefer women to have lower partner counts. It sounds to modern ears like “slut shaming” (a hilarious concept that tries to paper over the reality that the harshest critics of women who sleep around a lot tend to be… other women).

See point zero. The extent to which this applies to you depends to a considerable extent on your preferences.

If you aren’t jealous by nature, great! You can sleep around more in your early 20s and it won’t trouble you that your wife wasn’t a virgin when you met. I think jealousy is an understandable and common human trait, but the more common character flaw comes from having too much of it, rather than too little. If you don’t feel it, I certainly wouldn’t try to talk you into it. You’ve got a preference set that will pose you fewer hard tradeoffs in life. Happy days!

If you aren’t particularly into younger women, also great! You’ve got a much longer horizon in which to meet late 20s and early 30s women. Doubly so if you don’t want to have children. The budget constraint is thus considerably relaxed.

But if you do feel the above things, you might want to ponder such a tradeoff in advance. You’re probably going to have to give up something, unless you get lucky and meet a hot 18 year old when you’re 29 who’s super into you.

On average, by definition, people do not get lucky.

5. 

Gary Becker modeled the marriage market as being a matching problem. Men and women assortatively match on some set of traits, whether income, race, intelligence, attractiveness, or what have you. Gary Becker was a God damn genius, so I don’t mean to cast aspersions on this view. But I think there’s another aspect worth understanding that’s better described as an optimal stopping time problem.

If I had to sketch out the model, it would look as follows. Women come along according to some Poisson process. They are drawn from a distribution of quality and interest in you / compatibility. You can date each woman for some time period, during which you stop receiving a flow of new women. Your utility function is increasing in the number of women you hook up with, and with the average quality multiplied by the duration of the women you’re hooking up with. Finally, the average quality rate of the women you meet decreases with time, as per the point above. Your choices are a) which women to date versus reject, b) if you’re going to date them, for how long, and  c) when to pick a single woman to stick with for the remainder of your time period.

Solve for the optimal strategy.

One lesson from this is that the required quality threshold for marriage should be higher when you’re younger to settle on a person as a wife. This holds even if you know the true quality distribution, and would get worse if you were trying to learn about, e.g. how much is that I really love this girl, and how much is this just what nice long term dating feels like?

Another is that anything that increases the rate of meeting women (e.g. online dating) will have large increases in welfare. A lack of new arrivals is the biggest cause of failure to find a wife. If your life station is preventing this from happening, think very hard as to whether it’s worth it.

Yet another is that you should be particularly careful whom you “casually” date for extended periods of time, because this is going to reduce the rate at which you meet someone you might actually settle on. You will feel like you’re still single-ish, but if you’re not actively looking, you’re less likely to find someone.

Still another is that the greater your risk aversion, the more you’re going to settle on a medium quality partner early on.

But for our purposes here, the biggest philosophical difference is that the “optimal” part of optimal stopping time only holds in an ex ante sense. Once you stop, you’ll never really know what else would have come along. Unlike in a matching model where one sees the whole distribution, here you never do. Whoever you pick will always end up containing what ifs and uncertainties.

This setup also highlights the problem of having standards that are too high. I think this is another area where one can get mislead by with manosphere writings. It’s easy to enumerate a list of stuff that’s important in a woman, or stuff that’s a deal-breaker. Women do the same thing all the time, with their endless point checklists.

Rather, what’s hard is know the actual distribution of potential traits that you want, and which combination you might be able to plausibly get.

The “combination” part is especially hard. If you’re someone with options, you can probably score very highly on any one trait that you like in a woman. But the danger is in wanting too many traits at once, each of which is individually attainable. Even if the probabilities are independent, you start multiplying them out, and you realize you’ve got a pretty small chance of meeting them all.

The stereotype of bad women’s checklists is that they all want a 6’4 male model billionaire with rippling abs. But this understates the universality of the problem. The giveaway is “billionaire”, which is shorthand for “unattainable all on its own.”

Rather, the more pertinent problem is if you want a blond, 18 year old, hot, slim, smart Christian virgin with a sweet personality and a sense of humor (and I want to have banged a hundred girls before I met her).

This is the equivalent. But there’s not one single trait that gives it away. You probably could get at least any one trait if you really tried, or perhaps several. It’s unlikely you’ll get all of them.

This problem gets even worse if you fail to account for the likelihood that at least some of the traits you want are probably negatively correlated. For instance, one tradeoff I’ve noticed – being smart, and being easy going (broadly defined) are negatively correlated in women. Not hugely negatively correlated, but negatively correlated. Being smart tends to go with career ambition, and higher than average chances of teeth and claws ball cutting lawyer-like behavior. This is just one example. Being hot and smart might be another. Being hot and a nice person might be another still. When the world is willing to put up with all your b.s. because you’re very attractive, it’s hard to not turn into a bit of a b****. Having a high sex drive and low partner count is a definite one.

This is hard enough to forecast when you know the correlations, let alone if you’re not thinking about them.

Very few people in the manosphere write about which negative traits you should just lump it and put up with in order to compromise, because your wife is going to inevitably have things about her that you don’t like, just like there’ll be things about you that she doesn’t like. It doesn’t fit the “get irrationally overconfident!” vibe.

But I assure you that being irrationally overconfident that you’ll marry a blond, 18 year old, hot, slim, smart Christian virgin with a sweet personality and a sense of humor is not a recipe for winding up happy, if it causes you to reject all sorts of very eligible women who don’t meet that standard, and you only realise your mistake once your pool of options has shrunk.

Compromise is easier to stomach when you’ve got both tradeoffs in front of you, and you can see exactly what you get in return – in other words, when you’re choosing between two direct options. It’s much harder in an optimal stopping time world. Because you’ll have the lingering uncertainty that perhaps if you’d just waited longer and gotten a higher draw, the compromise might not have been necessary in the first place. This is the problem of the optimal stopping time psychology.

But if you set your standards high enough, you only end up with a wife if you effectively win the lottery. Or, even worse, if you win the lottery at the right time in your life, when your optimal quality threshold is sufficiently low that you’d actually take it.

6. 

The above is just one example of the point that the budget constraint problem is made much worse when the person doesn't realize that what they want is either impossible, mutually contradictory, or so negatively correlated as to be astonishingly unlikely.

To a psychologist, unlike an economist, the idea that people want impossible and contradictory things is not unusual. Rather, it's par for the course.

So what, in the generality, do men want?

I think they want three things.

First, they want to have a beautiful wife/long term girlfriend figure, who is sweet and caring, loyal and faithful only to them, that they can fall asleep next to at night and wake up next to in the morning.

Second, they want to be able to bang a wide range of hot young women on the side in a casual, no-strings-attached way, in a manner that makes them feel powerful and attractive (which, as I've noted before, rules out prostitution, which is begging for sex via the medium of money).

Third, they want to not feel like a hypocritical @**hole who goes around hurting those near and dear to them.

If you are lucky, you get to pick two out of three. Unless you are a sociopath, and they tend to have other problems. If you are unlucky, maybe you get one or none.

This is a fairly hard tradeoff. The number of women that are genuinely happy with a one-way open relationship is very few. The number of men who are genuinely happy with a two-way open relationship is similarly few.

This has an important lesson.

The hallmark of a good life decision is that it will probably feel vaguely unsatisfying, and there will always be a "grass is always greener" aspect. Beyond a certain point, the married man will vaguely envy the single man's variety of women. The single man will envy the married man's companionship and life certainty. The faithful will vaguely envy the freedom of the man with the selfish courage to have an affair or sleep with a prostitute. The cheater will envy the faithful man's ability to sleep peacefully at night and not have to hide his phone and lie about his whereabouts.

It is unlikely that the right decision will leave you with no regrets whatsoever, unless your preferences score very low on one of the three points above. Way down the line, one should not take the fact of vague regrets as indicating that you’ve made some mistake. The same problem exists on a smaller scale in any long term relationship.

7.

You’re thinking, “Come on Holmes, I’ve barely started in college. I’ve got better things to do than worry about either finding a wife now, or some weird scenario where I’m having difficulty finding a wife at age 40.”

Fine.

I can only end with the prompting to think further ahead, with a kind of empathy of what things might feel like at the time, and what you might do today as a consequence. This is not most people's default way of thinking.

This sounds very downbeat, but it’s not. Quite the contrary. Get it right, and you've got a lifetime of happiness ahead of you. More importantly, only in the fullness of time will you realise just how many options you had in front of you right at this moment, and how much possibility lay ahead of you. It’s an exciting time, and many is the old man who wishes he could be back in your shoes.

Good luck.

Your friend,

Shylock.