Why dating is so difficult

Why you should be sceptical of most dating strategies, except for one...

Throughout recent weeks, there has been a proliferation in dating advice. From the discussion surrounding whether you should request to hold hands to establish the parameters of the event, to what is the optimal pickup line, this is clearly a topic garnering nascent interest. Of course, one may think that natural selection, optimising for reproduction over the epochs, should make mating rather intuitive. So what explains the interest in strategies? How can we improve our success in this market?

A large part of why dating is such a minefield is that we are playing mixed strategy in a game of imperfect information, where signalling is pervasive. For instance, take the debate between Caplan and Hanania regarding whether to ask to hold hands. On one hand, asking such may signal a low confidence in one’s attractiveness, which is selected against in the dating market. It also “backs women into a corner” - a firm binary and irreversible decision in a scenario where romantic and sexual attraction often must be curated¹. On the other hand, asking such could be interpreted as a bold, courageous initiative to move the relationship forward; setting yourself apart from the other meek cowards.

Another aspect of the notorious difficulty of dating is that it relies on the exact language of non-verbal cues that men, relative to women, underperform in. This is also a large factor as to why no strategy can be dominant: women are remarkably more perceptive of the ‘true’ nature of a man than we grant credit for, owing to their comparative advantage in empathy and nonverbal language. Then the elephant in the room is that the males that consume dating advice are disproportionately likely to be autistic, which compounds these issues. Yet from this, my first piece of advice follows as a corollary. Be yourself.

Let me expand on what it means to be yourself. This does NOT mean that your attractiveness is invariant to your presentation or demeanor, so all of the usual self-help advice regarding working out or gaining social confidence or investing in your career or whatever should be listened to. One such piece of self-help advice can be found here. In general, the self-help genre tends to revolve around the trait of conscientiousness: delaying immediate gratification to improve our future life, or as us economists would put it, lowering discount rates. This is prosocial (discount rates correlate with a wide range of pathologies), and arduous to execute. It shows that you care deeply about yourself, and what better means to signal your attractiveness than that? All of these facets are attractive to women, and their level of attraction is determined by a man’s status, which is most improved (holding other key variables like IQ constant) via conscientiousness.

So no, to be yourself does not mean to be a bum. Rather, it means that it's surprisingly difficult to fool a woman. So if a strategy sounds too good to be true, it likely is. Otherwise, we would all pursue that strategy, leading to a pooling equilibrium in attractiveness failing to distinguish between the high vs low worth males. This would not be optimal from an evolutionary standpoint, hence dating naturally is governed by a separating equilibrium. This generates another corollary below…

To distinguish good from bad dating advice, the strategy must be costly and hard for all males (particularly the losers) to replicate. For this reason, I'm incredibly sceptical of most of the methods generated in the PUA community. Such online communities tend to be a haven for snake oil and grifts. Nonetheless, I also have immense respect for Neil Strauss and his followers. Why? Because they are at least making that initial effort, which is perhaps the most important aspect of dating…

What I like to refer to as the “dating market” is analogous to the labour market. Both are search and matching processes with endogenous frictions, as opposed to spot markets. In such markets, making that initial entry and pursuing as many matches as possible is how you maximise success. When applying for jobs, you apply to as many as possible, and by the law of large numbers, eventually via sheer volume alone, you will land an offer. The exact same principle applies to dating! Of course, just as with job applications, even the relatively competent or attractive candidates will face many rejections, so it's vital to recouperate from a disappointment. This means not fearing rejection in the first place. Much of Hanania's dating advice focuses on precisely developing that confidence. The core principle of the PUA community is not the specific methods per se, but in maximising matches and innovating upon failure, so basically viewing dating as how one approaches entrepreneurship. For this, it is essential to eradicate any transaction cost that could hamper your pursuit of matches, which entails simply not giving a fuck about how what you say makes you come across, or what other people think of you².

Derivative from this principle, this is why I like Ackman’s pickup line so much. No worries about “looking weird”, or hesitation about whether one appears to be a creep. A billionaire with an apparent deficiency in self-awareness at all. That's how you should come across! That is sexy confidence right there. I would modify his pickup line from a less vague term than “meet” to “date” though. This explicit, direct in requesting what you actually want with no deception nor hidden strategy, fits my advice to a tee:

‘Two days ago, I was leaving a supermarket in North London when a young man - I think he was 21, at most 25 - came up to me and said, “can I take you out on a date?”

I smiled, showed him the ring on my finger and said “I am engaged but if I were single, I would have said yes.”

I told him to walk with me for a bit and so we had a chat for about two blocks. Told him not to be shy and keep approaching women; I told how to look for signs of feminism that would derail the whole approach.

We see women now complaining that they get all dolled up for the night and yet men don’t hit on them. So I just tried whatever I could do to encourage this young man. I hope I didn’t give him bad advice.’

This, alongside the “black guy hitting on girls” philosophy, is how I will approach the subject going forward. If I see a potential candidate for my interest, no matter what the scenario is (with an exception being the workplace, where HR norms entail a lot more tact³), I will always ask that question. I will document my success with this going forward, and follow-up with this data in a subsequent post.

1. For this reason, I reject the claim that an initial “no” means you should stop pursuing her. Of course, this is one rather egregious example of a harmful relic of the MeToo era, which undoubtedly is contributing to the decline in birth rates. Obama had to ask Michelle multiple times before they dated, yet they're now happily married. Think of dating as part initial attraction, yet part investment into fostering such attraction. A corollary is that the friendzone is not necessarily static either, so resentment at being placed in such is often unwarranted. Nonetheless, you will garner a higher probability of success via focusing on matches outside your friendzone.

2. The perspicacious will notice a contradiction emerging with my advice to focus on self-help. My resolution is simple: you pursue self-help techniques because you care about yourself and your attractiveness for your own intrinsic sake alone, not because you care about how you're perceived by others. In fact, this intrinsic motivation is essential for perseverance here.

3. Such labyrinthine norms are baffling to me, which is why I find it easier to take mating out of the workplace.