Two years ago, Jacob wrote an essay about dating, sex, and loneliness. I found this essay recently because I am extremely interested in loneliness. It seems to me that a great deal of work is needed to resolve existential risk, and that loneliness is one of the top practical impediments to that work. I think that a good understanding and significant resolution to loneliness would be of enormous value to this community.

And so with that purpose in mind, I discovered Jacob’s essay. Jacob’s basic point, as I understand it, is that a trade-off exists between spending time opening to connection via self-work, and spending time opening to connection via relating. He sees a lot of his friends trying to open to connection via self-work alone, and in his essay he exhorts us to mix in some relating, too.

Jacob actually talks mostly about dating, not relating, but I do not think he would disagree with my re-characterization in terms of relating because he writes:

This essay is to tell you: [...] ask someone on a date. At the very least, invite someone to hang out and ask them what they’re struggling with.

Jacob’s essay is tenacious and charged, which I appreciate very much, but I am aiming for a different kind of charm in this post, so I will cut out some of the more charged language when I quote him, and I will indicate changes with square brackets. I promise to do my best not to skew the meaning of anything with my cuts.

Jacob's essay is at times harsh, at times gentle, at times crude, and at times sweet. All of these provoked things in me, which I appreciated very much. I have therefore found it most helpful to write this essay by simply quoting Jacob in full, and adding commentary. What follows is most of the original essay, with my replies inline. Jacob is in blockquotes, I am not.

Commentary

From Tokyo to TriBeCa, people are increasingly alone. People go on fewer dates, marry less and later, have smaller families if at all. People are having less sex, especially young people. The common complaint: it’s just too hard. Dating is hard, intimacy is hard, relationships are hard. I’m not ready to play on hard mode yet, I’ll do the relationship thing when I level up.

Jacob says that loneliness exists in the world, and is getting worse. Right in the second sentence he moves from loneliness to dating, marriage, and sex. I think this is significant. It is extremely common for people in our society to seek to overcome loneliness primarily through romantic connections. Why is that? It seems that friendship and family connections often "miss the spot" somehow. Why is that? I actually wonder if this is the true cause of loneliness.

This essay is to tell you: go [date] someone else. Ask someone on a date. At the very least, invite someone to hang out and ask them what they’re struggling with. This essay is not about how to make friends and lovers (a topic I’ll come back to), but an exhortation to actually go and do that. Now instead of later, directly instead of ass-backwards, seek relationships instead of seeking to be deemed worthy of relationships. [...]

I resonate a lot with this exhortation to get out there and really do it, not just in the domain of dating but in all domains. A similar ethos was expressed beautifully by Eliezer in many of his writings. The unnamed twelfth virtue of rationality was about bringing every ounce of one’s being into alignment with a clear purpose, cutting away all extraneous motion. This is not disconnected from Jacob’s point above.

But Jacob is making a more specific point when he says "seek relationships instead of seeking to be deemed worthy of relationships". This is vulnerable territory. I think what it really comes down to is that a certain amount of preparation for dating is good, but beyond a certain point perhaps preparation is being chosen over action because getting out there is quite scary. How do we overcome such fear? Well, one approach is to just go for it, with or without fear. This is the approach that Jacob seems to be advocating and it honestly has a lot to recommend it, but I would not advocate it across the board in every situation.

My argument doesn’t hinge on specific data relating to the intimacy recession and whether the survey counting sex dolls adjusted for inflation. If you’re reading [Jacob’s blog] as a brief escape from all the loving relationships smothering you, congrats! If you’re trying as hard as you can to connect and the world isn’t reciprocating, consider this essay as written for those you seek to connect with instead. [...].

Look, this paragraph is a little harsh due to the use of sarcasm in the context of such a vulnerable topic. But underneath that, I think Jacob is being quite reasonable and saying "hey, folks, come on, really, let’s get out there and do this". I get it. Sometimes the way to overcome hesitation is to just plunge in. Quantitative research can be useful, but it can also be a distraction from the main work.

Wherefore all this aloneness? The pink-hairs blame the red-pills who blame the pink-hairs. But really, they’re both in agreement that men and women are natural enemies and any interactions between the two are zero-sum. If you’re stuck in zero-sum thinking you’re probably on the wrong blog, but take this as a first dose of medicine and then go give someone a hug.

One level up from the gender war is the class war. Leftists blame loneliness on capitalism — single people buy twice as many toasters, sex toys, and Netflix subscriptions. Rightists blame socialism — for the state to be your daddy it must first destroy the family. I won’t spend much time on this. If your ability to connect with people depends more than zero on the GDP composition that’s the problem right there. "But in this economy…" Listen, if you’re struggling to build financial capital, maybe now is the time to invest in relationship capital instead?

There is a great deal being said here and with respect to Jacob I will attempt to deconstruct these two paragraphs a bit. Two underlying assumptions here are

1. Relations between men and women can be considered in terms of zero-sum versus non-zero-sum games

2. Relationship capital can be considered a kind of investment

There is a very important way in which these assumptions are helpful. First, there really is a certain game being played in dating, marriage, and sex, and it really matters whether that game is zero-sum or non-zero-sum. Second, relationship capital really does act like an investment, in that some effort goes in, and then over time that investment may bear fruits. But games are played in service of some kind of payoff and investments are made in order to reap some kind of reward. If daing, marriage, and sex are means to an end, then what exactly is that end?

It may also be worth considering the ways that the two assumptions above are unhelpful. We wouldn’t say that the Earth and the Sun are engaged in a game with each other. They just evolve according to the laws of physics. Relations between men and women could be viewed a bit like that. We also wouldn’t say that relations between a mother and a child, or between soldiers in a tight-knit platoon are always best-described as a game. There are times when you can open a side channel and transcend the game entirely. Relations between men and women could be viewed a bit like that, too.

The famous Atlantic article on The Sex Recession starts by noting that sex is now more accepted than ever: [...].

So why, in the words of philosopher Julia Kristeva, "everything is permitted and nothing is possible"?

I don’t think there’s a contradiction here. Everything is hard because it’s permitted.

There used to be no shortage of people who would judge you for having sex. Parents, peers, teachers, pastors, even the same media outlets that now claims to be "sex positive". And when you had to escape surveillance and risk judgment just to make out with someone, it was HOT. The illicit is sexy. Sneaking around created a bond based on a shared secret and merely having sex in the face of restriction was an achievement to be proud of. Having good sex was gravy.

When Jacob says "there used to be no shortage", is he referring to earlier times in our culture, or earlier times in our own personal lives? It’s true that sex had a particular edginess as a young person. Why exactly does that change over time? I think it’s because we become less present as we do anything a few times. The first time you go to a rock concert, for example, you are snapped into presence by the overwhelming novelty of the situation. At your second or third concert the novelty is less acute, and so the level of automatic presencing is less. But novelty is just one way to become present. There are other ways to become present. You can do it out of willpower alone, if you wish, or you can meditate or do yoga. So although transgression can be, as Jacob says, hot, it is not, I don’t think, the only way to find that heat.

If "the culture" no longer judges you for getting naked, who will? Your partner might. [...] This can be a problem, but it’s ameliorated by your partner repeatedly telling you that no, it was good, you’re just what they wanted. You should believe them. If they didn’t like you they’d make like Hamlet and ghost.

Now we’re discussing trust. Can we trust the words of our romantic partners? Can we trust that they like us, even when they say that they do? Perhaps we should trust their actions more than their words. It seems pretty plausible to me that trust is at the very heart of loneliness.

It’s hard to open up to someone that we don’t trust absolutely, and people in our lives demonstrate again and again that they are not absolutely trustworthy. It is the "absolutely" in that sentence that is key. It seems to me that indeed people in our lives are not absolutely trustworthy, because absolute trustworthiness is an extraordinarily high bar, so instead of trusting our friends and lovers absolutely, we should trust them in accord with out assessment of their trustworthiness, and that assessment is never going to come out at infinity.

There is a pattern that I have seen in myself and others in which one falls in love, decides to trust a lover absolutely, is eventually disappointed, decides never to trust anyone ever again, then due to the loneliness that ensues, eventually falls dramatically in love and decides once again to trust absolutely. This binary all-or-nothing trust just doesn’t fit the situation very well, and is premised, I think, on the mistaken assumption that true love requires absolute trust in another human being.

The big problem is when you start judging yourself. You can hide from your parents. You can find a partner who doesn’t judge your shortcomings. But you can’t outrun your own insecurities.

Well, this one is subtle. Suppose your friend comes to you and says "hey I think I have this particular irredeemable character flaw". Then you explain that whatever it is, it cannot possibly be irredeemable, because we always have a choice about how to react to our own flaws, and our choice about how to react is what character really means, so by finding a way to react virtuously to our supposedly-irredeemable character flaws we disprove their irredeemability. This is all well and good as far as it goes, but have you actually helped your friend? Suppose your friend now says "oh I see now that my irredeemable character flaw is that I believe in irredeemable character flaws". In this case you haven’t really helped your friend to escape from a belief in irredeemable character flaws, you’ve just replaced the belief in one particular irredeemable character flaw with another. So it goes with sentences like "The big problem is when you start judging yourself". This is essentially like saying "the big problem with you is when you start believing there is a big problem with you". It is recommending that you stop believing in big problems, while simultaneously pointing out a big problem.

The truth, it seems to me, is that we have the capacity to see our imperfections, and we have the capacity to work on them if we wish to. Sometimes we may not wish to! Some spiritual people look at this overall dynamic of seeing and working on imperfections as a kind of meta-level perfection. That is a nice way to look at things if you’re into that kind of thing. It shouldn’t be taken too literally.

It starts by comparing yourself to the internet. [...]. Everyone’s dates are more romantic on [the internet], their vacations sexier. [...]

It’s true that the things people post online are subject to a selection filter, and it’s true that this selection filter sharpens a particularly horrific form of suffering. This is deeply tragic. But selection filter or no selection filter, I think we should look carefully at what conclusions are being drawn from the comparison of our own dates and vacations to those of others. What is actually the line of reasoning we are using to go from these comparisons to whatever painful conclusion we seem to draw?

We might look at photos of other peoples’ dates and vacations in order to get ideas about places to go on dates and vacations. That seems pretty reasonable. We might look at photos of other peoples’ dates and vacations in order to share joy with our friends. That seems pretty reasonable.

Now, when we look at photos of other peoples’ dates and vacations, we might feel that our own dates and vacations are not as joyful as those of others. What can be said about this? Well, either we are mistaken in the perception that our own dates and vacations are less joyful than those of others, or we are not mistaken. What if we are not mistaken? Well, okay, in that case the dates and vacations of our friends are more joyful than our own. What actually does this imply?

Suppose I told you that there is this one monk who lives on such-and-such a mountain and has mastered equanimity to such an extent that she is almost always extremely joyful. Suppose I told you that I have watched your life and, just in case you wanted to know, it seems that you are, on average, less joyful than this one monk. Okay. So there is this one monk. Incredibly joyful. Great. What does this imply?

I think that the difference between the monk and the photos of other peoples’ dates and vacations is that with the latter, we wonder whether it is some irredeemable flaw in our character that is leading to the perceived or actual difference between our dates and vacations and those of others. This, so far as I can tell, is the epicenter of the pain, and, frankly, the most likely epicenter of loneliness. It is so painful to sit in contemplation of this irredeemability. To see evidence for it everywhere. To fight against it. To make heroic efforts to overcome it. To be bound up by it again and again. This is true suffering.

Yeah, this is real pain.

The pain is not imaginary, but the irredeemability is. It is based on a mistaken application of the agent model to ourselves, leading us to believe in the existence of an unchanging decision function within ourselves, leading us to trace the causes of our imperfect actions back to something that we believe is unchangeable. Under such assumptions, what would there be to do other than suffer? If this were how things really were, there would indeed be nothing to do. But this is not how things are. There is no unchanging decision function deep within ourselves. There is no place for any such absolute irredeemability to hide. The agent model is just a frame, and this is one of the places where it falls short.

Continuing on, Jacob writes:

[...]. People [...] start diverting all their energy into acquiring status markers, into being perceived as relationship-worthy by the real or imagined crowd of observers.

Here Jacob is discussing a vicious cycle in which the acquisition of a thing that never quite fulfills us leads to an ever-growing hunger for that thing in the hope that just a little bit more will finally fulfill us. He continues:

[...] As people spend more effort on status-climbing and self-improvement they spend less time in actual relationships. Unfortunately, you don’t get better at dating by learning to meditate or doing pushups alone in your room. When people who are obsessed with self-improvement have a miserable time on apps and first dates, they often conclude that problem is lack of self-improvement — surely when two well-developed high-status people effortless love will spark by itself! And so people keep chasing the next personal milestone. Get that degree, lose 10 pounds, learn that skill, read that book…

There is much that is good about self-development. It is not an evil pursuit, and I do not think that Jacob would claim that it is. Jacob is asking us to question what we are pursuing self-development in service of. If we are pursuing self-development in service of something that it can never fulfill, then we might get caught in a vicious cycle, always believing that we will get that thing with just a little extra self-development. It is as if we really really believed that drinking enough water would resolve our hunger for food. The more water we drink, the more convinced we become that drinking just a little more will resolve our hunger for food. But it won’t. It is not that drinking water is evil, it is that we’re operating on the basis of a straightforward misconception about what leads to what.

Self-development is good for many things. But, as Jacob points out, it may not ever give us an unequivocal feeling of worthiness. One possible reason for that might be that unequivocal feelings of worthiness just don’t exist. Another possible reason is that they do exist but self-development doesn’t lead there. Either way, if we are operating on the assumption that self-development will eventually lead to an unequivocal feeling of worthiness then we may end up in the vicious cycle that Jacob is pointing out to us here.

Self-development is riskless. Progress is slow but assured, and every step towards your personal goal is rewarded with likes and favs on social media. The pursuit itself raises one’s status. Opening up for connection, on the other hand, is scary. The rewards are great but so is the risk of failure.

I wouldn’t say that self-development is riskless. At a minimum there is a risk that one will fall into exactly the vicious cycle that Jacob is pointing at. But self-development can be less vulnerable than opening up for connection, because in self-development we can only be hurt by ourselves, whereas in relating we can be hurt by others, and I think what "vulnerable" means is existing in a state where we could in principle be hurt by others.

And real affection is the one thing you can’t brag about in a [social media] story. Intimacy for external consumption is not intimacy.

Yeah, the thing we value very highly -- real intimacy and real affection -- seems to be the thing most difficult to convey in a social media post. Why would that be?

And so, as the great guru put it: people want to be [highly developed] more than they want to [make love]. [Development] is capital. We seek to accumulate capital. [Making love] is labor. We seek to avoid labor. And so people are more [developed] than ever, and do ever less [lovemaking].

Our society places a lot of value, in general, on things that can be held onto. Self-development is something that we can hold onto. Making love is not. Therefore there is at least one reason to expect self-development to be prized over lovemaking. I don’t really know why this comparison is relevant, though.

In fact our society seems to value lovemaking a lot. And does anyone really view lovemaking as labor? I don’t buy this point. I’m not sure why Jacob is making it. He continues:

The pathological case of becoming obsessed with status and perception is when relationships themselves are subjugated to this end. When the main measure of a relationship is in how it makes you appear. Narcissism.

Indeed. Self-aggrandizement certainly seems like an unhealthy thing to pursue relationships in service of.

Narcissists ask: How does this relationship reinforce my ego narrative brand? How worthy does it make me seem? Ego-poisoned people who are short of narcissism merely ask: Would I be judged of a relationship? These questions are self-focused, and intimacy requires that you relinquish them entirely. Instead, the question that starts all good relationships is: Can I make someone happy?

Well said. Can I make someone happy?

Making someone happy doesn’t imply forever, or as happy as they can be, or happier than anyone else could make them. A compliment makes a person happy. A text where you share something fun. Being a good listener on a date even if you didn’t blow their mind with electric conversation. A cuddle makes a person happy even if it stays a cuddle. Sex makes people happy even if it’s not [mind-blowing].

Why did we go from asking whether we could make someone happy to asking whether we could make someone happier than anyone else could make them? Jacob is pointing out here that the answer to this question isn’t really relevant, but why did we choose to turn our attention to this question in the first place?

When a niggling thought like "yes my partner is happy but perhaps another person could make them even happier" bothers us, we basically have two choices: either we can turn towards it and take the question so seriously that we see right through it to the other side, or we can turn away from it and stop paying attention to the question at all. I think it is when we choose neither one, and stay in the no-man’s-land middle ground, that we get pummeled by it over and over.

Jacob continues:

Romance is the most complex and rewarding multi-player game that humanity has invented. There are many romantic interactions that are short of your wildest dreams that are still worth having, that make two people happier than they would have been alone. And if you’re starting out, that’s where you should aim for.

There is a background assumption here that romantic interactions can be put into some kind of ordering, and there is a second assumption that people gain experience and have romantic interactions that rank higher and higher in that ordering. Perhaps these are true, but they seem to conflict with the earlier point about romantic interactions being more intense during early periods of our lives.

I do not really buy that there is an ordering over romantic interactions that is worth paying attention to.

Dating and sex and relationships are all trainable skills. You learn by doing. To learn painting you start by making 100 paintings. To get good at tennis you start by playing 100 matches. The first 100 will be mostly mediocre and some will be outright bad, but the 101st one has the chance to be good.

But unlike tennis and painting, our first experiences of romantic love are often unbearably sublime.

Dating and sex and relationships are all trainable skills. You learn by doing. To learn painting you start by making 100 paintings. To get good at tennis you start by playing 100 matches. The first 100 will be mostly mediocre and some will be outright bad, but the 101st one has the chance to be good.

To go on a great date, you have to go on 100 mediocre dates. Or at least, put yourself in the mindset where that is your goal. That is how you learn to date and make people happy to be dating you. You learn how to deal with rejection and breakups and how to bounce back. Just as importantly, that’s where you learn to enjoy dating (see rule 97).

The sentence that most sticks out to me here is "that is how you learn to [...] make people happy to be dating you". It’s difficult to write about this. I think the best way forward is to look at background assumptions and try to apply them consciously when they are helpful, and not apply them unconsciously when they are unhelpful. Throughout much of Jacob’s essay I sense a background assumption of a kind of game theoretic approach to dating. This can be a beautiful way to see things because when we see the whole game that we are engaged in then we can jump right to the equilibrium move, rather than being pushed there slowly and painfully by trial and error. Where then does this game theoretic way of seeing things fall down? Very simply, I think it leads to a lot of anxiety. Overall, I think it therefore makes sense to use this game theoretic frame more than zero but not excessively.

Now there is a very important background assumption that I am making here, which is that we can choose our own thoughts. The way I see it, we cannot exactly choose our thoughts on a moment-by-moment basis, but we can exert considerable power over our thoughts by directing our attention to certain topics, by practicing concentrating on one thing, and by setting up our external environment to reinforce certain trains of thought and not others. Using these mechanisms I do think we have the power to choose how much to engage with a game theoretic frame in dating.

Jacob finishes with a final exhortation to get out there and date:

Perhaps there was a hidden benefit to the premodern mating context when you had roughly one shot at a successful partnering — all you could do is invest in the one relationship you’re given. But now that the option to date without lifelong commitment exists it affects your dating life even if you don’t plan on it. The option is always there for you and your partners. Waiting until you hit some life marker to start dating just means that you miss out on years of learning what other people are looking for, and what you yourself are looking for in a relationship.

And if you’re too busy for dating, actually busy with something that’s more important to you than romance, consider that dating doesn’t have to be a sink of time and energy. A casual date can be invigorating, and a partner can provide the support you need in your struggles.

So go out there and make some people mildly happy by going on mediocre dates[4] and having mediocre sex and learning to connect with people romantically instead of having your head up your own ass. There are more interesting things to put in there with a partner.

It’s a beautiful sentiment, isn’t it?

Conclusion

Well, what can be said of all this?

First up, there is really a lot going on here, not just in Jacob’s essay, but on this topic in general. There is social commentary, political commentary, economics, game theory, intimacy, happiness, self-development, life advice, and a host of background assumptions to go along with these. When it’s hard to make sense of something, I find it most helpful to get really clear about my purpose, and my purpose here is to understand and resolve loneliness. What have we learned about the causes of and resolution to loneliness?

The first question, I think, is whether dating, marriage, and sex is a plausible way out of loneliness at all. Is it? I don’t know.

The second question is, well, if we do want to pursue dating, mariage, and sex, then what is a good way to pursue it? Jacob argues that we should pursue it by practicing it. Well, OK, that sounds pretty reasonable.

The third question is, well, if we don’t want to pursue dating, marriage, and sex, then what is loneliness and what is the way out of loneliness? I don’t know.

It is interesting to me that writing this essay has been difficult but not lonely. Here I am, sitting alone in my room, writing an essay about loneliness, and yet this experience right here actually is not loneliness. This is fun, and I think that it is good, too, because loneliness really is an impediment to getting things done, and there really are some darn important things to get done in the world, and so it really does makes sense to investigate loneliness, and one pretty good way to investigate loneliness is to write about it and discuss it with friends in the comments.

Perhaps the end of loneliness lies in clarity of purpose.