The Prisoner's Dilemma: Trust, Relationships, and Risk

Written by
Garrett Dailey

The Prisoner's Dilemma: Trust, Relationships, and Risk

Written by
Garrett Dailey

The Prisoner's Dilemma: Trust, Relationships, and Risk

Written by
Garrett Dailey

After my long hiatus, I’ve come to a few realizations. First, while I was originally going to do Year Three of MasterSelf as predominantly about aesthetics, it’s actually not (or at least, shouldn’t be) that hard to understand that beauty=good and modern art pretensions=bad, so that’s not happening. Second, if we’re moving past aesthetics, that brings us to ethics and politics, or: how to pursue your values and how to navigate values in a world full of people, respectively. With that in mind, we’re going to start with a famous game theory thought experiment, the Prisoner’s Dilemma. Along the way, we’re going to see what this has to do with relationships, evolution, and more.

Let’s get it.

The Prisoner’s Dilemma is presented on Wikipedia as follows:

Two members of a criminal gang are arrested and imprisoned. Each prisoner is in solitary confinement with no means of communicating with the other. The prosecutors lack sufficient evidence to convict the pair on the principal charge, but they have enough to convict both on a lesser charge. Simultaneously, the prosecutors offer each prisoner a bargain. Each prisoner is given the opportunity either to betray the other by testifying that the other committed the crime, or to cooperate with the other by remaining silent.

The possible outcomes are:

  • If A and B each betray the other, each of them serves two years in prison
  • If A betrays B but B remains silent, A will be set free and B will serve three years in prison (and vice versa)
  • If A and B both remain silent, both of them will serve only one year in prison (on the lesser charge).


What we have here, in essence, is a system in which fear disincentivizes trust. This is really important to understand. We have the knowledge that your prisoner counterpart is a criminal (as are you, but we tend to imagine we’re the hero of our story, right), and thus, is a fallible person who may act against your interest. In fact, they’re given incentive to violate your trust, because if you don’t rat and they do, they get the best outcome (assuming that the best outcome is not going to jail, but we’ll get to that later). If you both trust each other, you both go to jail, albeit not for as long.

This is great and all, but how does this relate to anything useful in our lives? What if I told you that human relationships in modern times are basically the Prisoner’s Dilemma?

Here’s the difference- the Prisoner’s Dilemma is a one-time game with two players. Modern relationships are actually like the Prisoner’s Dilemma but with (effectively) infinite players and infinite rounds- there are plenty of fish in the sea, and you can continue playing until you either die or take up celibacy (voluntarily or otherwise).

We’ll call this the Iterative Prisoner’s Dilemma for the sake of science, but for our purposes, it’s just the modern dating scene. Here are the critical differences:

First, in the original scenario, A and B are obviously the potential romantic partners. In modernity (as well as antiquity, but that’s not the game we’re playing at the moment), there may also be nonstandard numbers of players- you can get some polyamorous nonsense, or polygamy, or polyandry, but that’s not anything I care to cover here for what should be obvious reasons. This isn’t Tumblr.

Second, because this game includes all the active players (people seeking relationships) and has infinite rounds, we get something the original Dilemma does not have:

A scoreboard.

One version of this statistic would be the divorce rate, but that excludes relationships that don’t turn into marriages. In reality, we don’t have a hard statistic to measure the overarching results of our iterative dilemma, but the cultural attitude towards monogamy (or relationships in general) is going to reflect it. Currently, the odds of a marriage ending in divorce are something like 40-50%.

We can rewrite our iterative relationship dilemma (alternatively, Prisoners of Love Dilemma, groan) as:


Two members of society are attracted and infatuated. Each person has a private internal experience (solipsism) that is ultimately a mystery to the other. If each person is honest with the other, the relationship has the highest chance of succeeding, although both will have an emotional investment, making them vulnerable if it fails. However, if one person is not honest, they will avoid vulnerability, but the other will suffer greatly. Each person is given the opportunity either to betray the other by being dishonest and protecting themselves, or to cooperate with the other by being honest.

The possible outcomes are:

  • If A betrays B but B was honest, A will move on and B will suffer both the loss of love and the accumulative state of cynicism (and vice versa)
  • If A and B each betray the other, each of them will get accumulatively more cynical and be lonely.
  • If A and B are both honest, both of them will acquire emotional investment and risk pain, but their relationship has the highest chance of success.


Additionally, the outcome of each iteration of this dilemma contributes to the individual’s future strategy, the local average, and the overarching game’s average success and failure rate.

Investigating the Causes and Risks for Divorce - Alliance for Marriage


Okay, that was a lot of technical stuff, let’s simplify. Any time people cheat, the prejudice against future partners sways towards mistrust. Any time a relationship fails, the culture believes in them less. This is important for several reasons.

Relationships do not exist in a vacuum, like the original Dilemma does. Every person is informed by the relationship their parents had, the preexisting cultural conception of what relationships are, and their own accumulative experiences (once bitten, twice shy.) If your parents got divorced, you’re not set up for success, as per Wolfinger (2003):


“People from divorced families often marry other children of divorce. This phenomenon, which I call family structure homogamy, persists across a variety of sociodemographic boundaries. In addition, I replicate earlier research by demonstrating that marriages between two children of divorce are especially likely to fail. These findings shed new light on the intergenerational transmission of divorce by showing that people from divorced families often marry under conditions that bode poorly for marital stability.”

Basically, you inherit some bias from your parents, consciously or otherwise. This isn’t just a game with players A and B, but with AB and CD (the kids of A + B, and C + D, respectively). Our culture actually retains this information over time: television and movies begin to reflect the success and failure rate of the world we live in as more characters are divorced, and that rate actually begins to change the game at scale.

Now, we have to address one of the fundamental assumptions that I made in my version of the dilemma- what if the goal for current players is not a mutually fulfilling relationship? Certainly, there are plenty of people who aim for promiscuity, one night stands, or one short lived relationship after another. Do these people not want to fall in love?

Well, despite what popular culture seems to indicate at times (I’m looking at you, “thinkpiece” blogs that will not be named that my readers can almost certainly identify), I tend to think that most of these people are A: lying to themselves and B: emotionally stunted people embracing their defense mechanisms as normal. That’s a bit of an audacious statement, but I’ll make it because that definitely describes me for some length of time after negative relationship experiences.

The first round of the dilemma (broadly speaking) has the highest odds of success because we lack the accumulated cynicism, but the dilemma is almost always asymmetric- it might be your first time playing, but not the other person’s. This is a large part of the present difficulty, since we’re reaching a point where more people have been burned than not, but we’ll come back to that in a bit. If you get lucky, you win on round one and you live happily ever after. Hooray.

If not, though, the plot thickens.

If you’ve ever seen a man get punched in the face unexpectedly, you’ll know that part of the shock response to painful stimuli is that you recoil defensively basically automatically- it’s a reflex. If you haven’t, I recommend you go watch it, it’s good fun. If you’re considering punching a man unexpectedly, record it, and good luck. This should not be construed as encouragement, for legal purposes.

A failed relationship has a similar effect to being punched, although potentially in a more sensitive area, and sometimes instead of it being a surprise it’s a protracted, slow motion car crash. You’ve seen these sorts of things, I’m sure. At any rate, after a failed relationship, we tend to recoil defensively, and this is where things become problematic.

If a kid is learning to ride a bike and he falls down as soon as you take the training wheels off, the kid is probably going to be disinclined to get back on the bike. That’s natural. However, if he never tries again, that’s less so.

The problem in modernity, however, is that we don’t just fall off the bike and decide not to ride again. We actually fall off the bike, blame the bike and Lance Armstrong and the whole damn Tour de France for existing and giving us this false perception of how cool bike riding should be, and then we rationalize out a whole philosophy that says that we shouldn’t fall into the trap of wanting to ride bikes because it’s emasculating.

This presents a problem.

The issue is that we’ve accumulated so much cynicism that the odds are fairly high that most players cannot or should not be trusted- the cultural values have shifted due to so many of the players being jaded and either being the children of failed marriages or having failed themselves that everyone has begun to stop believing it’s possible to have a successful relationship at all. In psychology, they call that projecting, but it’s significant enough that most of society is projecting because what everyone believes creates the social reality, whether it’s true or not.

I’ve spent a significant amount of time trying to puzzle out this seemingly intractable problem, and one of the things I came to the realization of in the process was that a large part of our relationship insecurities is a projection of our social insecurities. Our world is not stable in the way that it used to be, and stability matters, remember that for later. Back in the day (he said, like some kind of Boomer), you could get a job and keep it for life. Nowadays, I personally have had like 15 jobs in about 10 years of employment.

Things are changing.

Part of the issue is that people themselves change, and they aren’t the same as they were at the beginning of the relationship, sure, but I’d actually say that the issue there is more that most people have the emotional maturity of children (and I’ll volunteer myself as an example here, too, it’s hard work). People may change, but the fundamental human experience doesn’t change so quickly. Biology has been the same for ages, it will likely be mostly the same for many ages more.

I’d go so far as to argue we’d have to make some kind of a biological argument for marriage (or at least monogamy if we’re speaking broadly) as a good thing. Many people aside from myself have tried many variations on this, for or against, so I’ll be brief.

Most of the arguments for non-monogamous pairs argue more for the reproductive potential of the individual in the sense of them propagating their genes- a man can have tons of kids like Genghis Khan. I would argue that monogamy wins for a few reasons- your kids come out less likely to die in childhood, you’re less likely to have your mate stolen, and what I think is likely the most recent, the most important, and would guess is the least well-researched:

Fathers have a tremendous impact on the lives of their children.

In a non-monogamous child-rearing setup, surrogate fathers or boyfriends of the mother have the highest rates of abuse (remember what I said about your kids being less likely to die?)- there’s an evolutionary predisposition to kill kids that aren’t yours because they steal resources, and whether that’s horrible to hear or not doesn’t change the stats of child abuse that reflect it. We have a lot of built in things that prevent us from killing our own kids that don’t apply to other people’s kids for this reason. From the National Center for Health Research:

“A 2009 study by Lawrence Berger and colleagues examined whether Child Protective Services (CPS) involvement varied based on a man in the mother’s life.[1] Using data on 2,297 families from the Fragile Families and Child Wellbeing Study, the researchers categorized relationships according to whether the mother was living with a (male) partner or spouse, was involved in a dating relationship, or was not romantically involved.  Families in which the mother had a partner were further characterized by whether her partner was the biological father of none, some, or all of the children in her household.

Results of the 2009 study showed that families living with a man who was not the biological father of all the children in the home, and families living without a man in the home, were significantly more likely to be contacted by CPS compared to families in which the biological father of all the children lived with the mother.”

One of the things I find really fascinating is the fact that some species lay thousands of eggs at once, and most of them get eaten before or just after hatching. Humans, of course, can only have one (or rarely, a few) kids at a time, which indicates that our move towards quality over quantity of offspring has been the case for ages.

There is one thing that’s worth mentioning:

A certain amount of human history involves kings who had way, way more (like Genghis-Khan-level more) kids than most people, and in these eras, many men did not reproduce at all. However, I think this was due to asymmetrical physical prowess (sexual dimorphism as well) combined with asymmetrical access to technology. Kings could fight, raid, get rich, buy better gear, and protect/provide for large amounts of women and children. That being said, it seems that technology has made that asymmetry less pronounced- doesn’t matter how strong you are, no one is bulletproof, and the invention of firearms basically eliminated the swordsman who trained his whole life to fight that enabled the asymmetrical king/kingdom hierarchy.

While it seems that for any one male the ideal situation may be to just have such a prodigious quantity of offspring that they can outweigh the downsides of having kids that get no paternal attention or resources, it does not seem to be sustainable at scale, and it also seems that people end up overthrowing kings, too. Harem seeking is actually extremely antisocial, and maintaining a harem requires some kind of social backing (soldiers to guard your concubines, or eunuchs, which, aside from the numerous who are mentally castrated, are even less common in modernity.)

Anyway, that’s a bit of a digression. If you want to read more about the evolutionary aspect, check out The Red Queen by Matt Ridley.

To summarize:

For most people, most of the time, you are going to have the best luck by having monogamous pairs and raising your own kids. Basically every other form of relationship is bad for kids, we seem to have some evolutionary bias towards people who raised their kids with both parents around and invested, and those kids have higher degrees of trust, which builds social cohesion. On the other hand, if you are feeling particularly tough, you can try and take over the world and create a harem, but the likelihood of that is slim and, strangely enough, other dudes don’t usually like helping you defend your harem.

Back to the Dilemma:

As I touched on in Beyond the Masculine and Feminine, as well as the Syzygy series, one of the things that we really seem to want to ignore is the fact that life is meant to reproduce itself, and under that assumption, relationships should exist with the goal of having kids that aren’t ruined by your behavior in mind. I know from experience most people do not operate that way, and you probably felt that was a bit of a nonstandard statement in the context of modern society,  but it’s true. It doesn’t matter how your relationships go if your kids are fucked up- or if it takes 10 generations for your actions to fuck things up for your kids. If you don’t have kids, evolution doesn’t care what you think.

Beyond all that technical, evolutionary talk, there is one thing that’s truly significant here: the concept and experience of Love. We evolved the ability to feel an emotion profound enough to have resulted in the creation of most of the art and other works you care about, but modern man in his astute brilliance wants to say, “oh, love is just a chemical reaction, it’s not real.”

Being pretentious as a self-defense mechanism also seems to have some evolutionary bias towards it, too, so unfortunately I doubt that’s something that will go away anytime soon.

I would argue that the majority of our modern issues, especially isolation, stem from a turning-away from Love as a value. We’ve cheapened our relationships, and, in hiding from risk, we close ourselves off to the possibility that we can share in the pinnacle human experience that is Love. This brings me to the strange and interesting product of this article- how are we meant to reverse the progression of the Iterated Prisoner’s Dilemma towards cynicism?

We have to approach relationships with the knowledge that we’re going to be hurt. Not to think we might, but to know and do anyway. All of our modern aversion to opening ourselves up is out of the fear of possible pain, but as we understand from the dilemma, we cannot win if we are not honest, we just lose less.

More simply, either play to win or don’t play at all.

We must accept that pain is not only necessary, but inevitable. We have to learn to suffer in the pursuit of something greater again, and only when we’re willing to suffer for this greater ideal do we even have a chance to succeed. If you aren’t willing to lose, you’ve already lost. If you aren’t willing to lose, you won’t ever win.

Stop lying to yourself- accept that you want to love and be loved in return, don’t deny this fundamental human experience, and offer yourself up to be sacrificed on the altar. Otherwise, the world continues in this half-life of noncommittal, self-protected disinterest that is very clearly killing us.

Seek life, seek Love, and take the risk.