Ready, Player

Don't play by the rules — play by roles

Recap of last week’s post: the reason people so obsessively opine, gossip, and moralize about dating is that they’re desperate to figure out the rules of the dating game. But the rules discourse add no clarity for the clueless. There are few universal rules — dating norms are local — and in either case those who discourse the loudest are often the least wise.

The easy takeaway here is to pay less attention to “dating discourse”, or at least to not take any global proclamations as a personal guide. But that still leaves you as a clueless person trying to date other clueless people. How are you supposed to figure out the rules of a game if the other players don’t even know them?

Here’s the secret: rules only exist in games with referees — a third party that controls your dating destiny. If you’re a rural Indian, Hasidic Jew, or 14th Century princess, your dating life depends on your parents, matchmakers, or the King’s political exigencies. They get to set rules for your dates, for example: that your horoscopes align, that you don’t share a name with your spouse’s parent, that your patron saints are compatible. If your own dating life had hard and fast rules, you wouldn’t be confused about this. You would be taught the rules by those who enforce the rules on you.

There are the basic rules of being a decent human, and these apply doubly to dating: don’t lie, don’t use violence, don’t betray trust, don’t blame others for your own shitty choices. But again, you shouldn’t be confused about those or need to glean them from Reddit flame wars.

When two decent humans meet who are free to date or not to date with no arbiters, dating isn’t about playing by the rules. It’s about playing your roles.

Yes, And…

Improvisational theater, or improv, is a rather unusual activity. There is no script or rules or metrics to judge it by, but everyone can tell a good scene from a bad one. Improv is a form of acting, but one in which listening is more important than speaking. Improv is scary and funny. You can practice improv for decades, but you can never be fully prepared. Improv is about creating something new and unique, something that didn’t exist before and won’t be replicated again.

Dating is improv.

Understandably, this makes a lot of people upset. These people sometimes keep demanding that I give them universally applicable dating instructions, even after I spent a month explaining that it won’t help. If I tell these people that dating is improv, they demand universal instructions for doing good improv.

There is only one instruction, the same for both dating and improv. It is in Leviticus 19:18:

do not bear a grudge against your people, but love your fellow as yourself¹

There are general guidelines to doing improv well. The one about grudges is important: teachers often say that there are no mistakes in improv, only new opportunities. It’s not even about forgiving your partner if they mess up, but rather about accepting that anything they do is now part of the new scene you’re building together. Don’t come onto the stage holding preexisting grudges!

The principles of improv you learn in class are flexible and suggestive. The only person who can give you specific instruction is not your teacher or the audience, but your fellow actor in the scene. Let their will become your will in each instant, without holding onto the past or drifting off into planning the future.

I would add one important item to the list of ways to practice flirting by doing things you enjoy more than flirting. If you’re someone who enjoys practicing mindfulness meditation, you can practice focusing your entire attention on the present moment and the one person across from you. You don’t need to do anything or achieve anything, just let everything that isn’t just now and just them float freely out of your awareness. If you can do that, you possess a flirting superpower.

Role Model

The yearning for a clear set of rules to follow is a trap for both women and men, but for different reasons.

For women, because it feeds into the anxiety about being socially judged. This anxiety only grows and becomes overwhelming when no clear agreed-upon set of rules can be found. When young women insist that men may only ask them out on apps and never in person, it often means: don’t ask me out where other people would observe and judge my reaction, I don’t know how I’m supposed to react!²

The trap for men is that they are expected to be the proactive, agentic party. But, searching for rules in the discourse, a man will find 10 DON’Ts for every DO. All prohibition and no instruction. When women say what they want from men they are usually talking about a very specific guy. If a man tries to follow all these demands at once, he would find his space of allowable actions constrained to nothing at all.

Rules are rigid, impersonal, and fake. Roles are fluid, relational, and useful.

Here’s a great thread by Matt Bateman explaining how he learned to love playing the man’s role in courtship, and what it actually means (emphasis mine):

A story about learning a masculine role in relationships, that may perhaps be useful to people similar enough to me. […]

My problem was courtship.

I “did fine” in terms of having girlfriends etc.—generally managed to date the girls I wanted to date, and in any case wasn’t an incel. But it always felt awkward to me. Like, how-is-this-supposed-to-work awkward. I managed to awkwardly situate myself into (and out of) relationships. They weren’t something I pursued like I pursued other goals. I got better at other things in my life, I wasn’t really getting better at relationships. I might have been getting worse at them.

I pondered romcom/sitcom-level things such as “guy is supposed to make move, guy is supposed to propose, guy is supposed to ‘lead’; girl is supposed to signal availability/interest, girl is supposed to gatekeep”, etc. After some thought I was like... yeah ok I’m good with this. […]

And just like that: I was unblocked. I could ask girls out, I knew what to do on dates, I knew how to handle breakups, I was more comfortable with additional things in this vicinity better left to implication. I won’t say I was good at these things. More just that I considered them to be, happily, my job. And so it wasn’t awkward anymore, even when I wasn’t good at them. What’s worth doing is worth doing badly, or however the saying goes.

Whenever it felt like I was waiting, or things were coasting or simmering for too long, or it was unclear how to proceed, I would now think: oh right, I’m supposed to read the room and do something here. That’s my role in the game. That’s it, that was the unblock.

I think there’s an equivalent if you’re on the girl-side of the standard game. Something like “my role in this game is not to do something so overt, it is to prepare the room to be read, it is to issue and rescind invitations, it is to enable/handicap further moves” etc.

When Matt thought of gendered expectations in courtship as arbitrary rules contrived by bygone civilizations, they were merely an obstacle. When he saw them as guidelines giving both men and women a starting point to play the game from, he was excited to play.

So what exactly is each gender’s role? Matt is wisely keeping it vague in the thread, but we can generalize.

A man’s role consists of:

1. Actively reading the situation, noticing the woman’s signals and indications of what is welcome and what isn’t.

2. Taking the initiative when the situation is stagnant, even if there isn’t perfect clarity on the best way to proceed.

3. Issuing explicit invites to various courses of action, and thus opening himself up to being the one who’s explicitly rejected.

4. Accepting the woman’s judgment as she welcomes or rejects an invitation, setting up the subsequent scene.

A woman’s role is complementary:

1. Setting the emotional tone and context of a scene.

2. Providing encouragement or caution with subtle cues and signals.

3. Choosing whether to reject an invitation or follow the man with enthusiasm.

4. Maintaining harmony and grace throughout, protecting everyone’s feelings and reputations.

Let’s explore the simple example of texting after the first date. The rules say: wait 3 days to not seem desperate but also text the next day to show interest and send two texts to say last night was fun and continue the conversation but also never double text and also the woman should text “got home safe” but also if the woman texts it’s over. LOL rulebros BTFO.

The roles say: texting after a first date is an explicit invitation (to continue texting) and thus generally falls within the men's purview. The woman's role is to signal what course of action she's amenable to towards the end of the date. If she emphasizes being busy and keeps the conversation light, she's curating a more casual scene; the guy should respect that by waiting a few days and keeping future texts focused on concrete plans. If she shows particular enthusiasm about shared interests or future possibilities, she's inviting a more immediate connection; the guy should follow up the next day with something specific ("here's that Second Person article I mentioned!"). And if he's uncertain about her interest, his role is still to make an explicit move that gives her a clear chance to welcome or reject it - not an "I had fun last night!" but a specific invitation she can respond to.

Compassion for the Clueless

Playing a game with no rules is hard. People are bad at it, especially when most of us don’t realize exactly what the game is and what we want out of it. We mess up, change our minds, send mixed signals, ignore clear messages, passively wait for instructions, and get frustrated with the other person for fucking it up.

What if you get it and the other person doesn’t? You’re still playing the game. I wrote about improv previously:

The best thing about improv is that you can practice it with people who have absolutely no idea it’s happening. Most people most of the time are playing out some scene with tropes and roles and status relationships. You can just “yes, and” and join it. They won’t stop you.

You can practice inhabiting the roles others cast you into or subverting them, creating awkwardness and returning to grace, reveling in conflict or resolving it.

If you’re trying to date someone who is awful at the improv game, that just folds into improv. Do they reject traditional roles? Cool, you have more freedom to improvise. They insist on strict rules? Nice, it sets a clear structure for the scene. Do they constantly waver, not knowing what they want and how they want it? No matter, you’re only focused on the present moment anyway.

If you know who you are and what you’re looking for, you’re playing on easier difficulty than someone who doesn’t. And if you stick with what you’re doing, they will eventually figure it out as well. We are all born actors, looking for a role that fits. The best moments in improv theater come from salvaging awkward situations. The same is true of flirting — the hottest thing you can do is rescue them from themselves.

The clueless deserve compassion. It’s easy to apply this lesson to the other person, especially if you are really attracted to them and know that aside from their cluelessness they are wonderful. It’s just as important to apply this lesson to yourself.

There are many ways to not play the game. Yearning for a “return to tradition” of saints-based matchmaking. Waiting for a soulmate to somehow fight their way through your general apathy towards the opposite sex. Striving to convince the online discourse that you alone are worthy and underappreciated. There is little risk in these, and no reward.

If you feel you don’t know how to play, that means you should have started yesterday. That’s okay, hesitation also deserves forgiveness. Forgive yourself and get in the game today.

1. The King James translation of the object of your love as “neighbor” is mildly infuriating in the violence it does both to the connotations of the original Hebrew and to the context in which it was written. That “neighbor” (etymologically: nearby + boor) has come to mean “fellow” and to carry a universalist connotation is downstream of this Christian reinterpretation of what was originally an isolationist code of ethics for a particular tribe.

To wit, the female form of רע (rea), the Hebrew word translated as “neighbor”, is רעיה (raya). It means “wife”, not “the girl next door”.

2. And guys saying “I can’t ask women out in person, I’ll get canceled” are coping for their own social anxiety.