If That Makes Sense #11

On the rules of dating, playing games, emotional protection and the true fun of it all

I was seeing a boy for a month, and we ended things recently: I was still very into things, but he had checked out - emotionally, at least. This, crucially, hasn't happened to me for as long as I can remember: feeling some kind of way for someone after such a short space of time. I know it's good to protect oneself emotionally, and maybe I forgot some of my own rules in the span of the pandemic when I was doing nothing, but why are we so desperate to hand wring over the timing of things? Instagram messages, WhatsApp texts, the days between dates. It's all so arbitrary. Don't we vary from person-to-person? Why do we have rules and games? Why is playing hard to get deemed such a necessity?

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The biggest regret of my dad’s life is that I don’t play chess. He’s told me this before, many times, but he also doesn’t have to – because whenever I talk about anyone I am dating, he asks me if they play chess. If they don’t, he will begrudgingly put up with it (and I am an adult so, really, why am I even mentioning this it’s not his business at all), but if they do, he approves. I used to think he was joking when he said this but he still says it: he says that if you can play chess, you can play life. 

I do hope and think this is a bit too simplistic and can confirm I have met some terrible people who play chess. But there it is – the game. Chess is (now bear with me, per my previous paragraph I don’t really play) about thinking three, four, five steps ahead at all times. You’re not just anticipating the next Instagram message or the hours until you ask them out again, you’re adding both together and multiplying that by the probability that they hated your last WhatsApp and will not be free next Friday because of that thing you said four days ago. Or something like that. 

Like you, I dated very little during the pandemic and kept yelling to everyone who would listen that I was “FINE if not very EMOTIONALLY BORED”. This meant that when the prospect of dating returned a couple of months ago I thought that surely I was in a calm, measured, mature, infinitely wise place where those rules had been obliterated during these Unprecedented Times and everything would be fun and easy and good because we all had lots of lost time to make up for and when you’ve been robbed of 15 months of your life you kind of lose the impetus to wait 6-12 hours to text someone back. I’d love to tell you that that’s what happened, but then you wouldn’t be receiving this email today. 

Illustration by Anna Boulogne

Why do we have rules and games, you ask? Great question! Let me know when you find out. If I had an answer it would be like being able to tell you how to turn a five-hour game of Risk into 15 minutes. It would be insane and impossible and, to be honest, not really fun anymore. It is so difficult and often ends in tears, but there has not been a year of my life when I have not felt the intense desire to fall out with everyone I love over a game of Risk. Am I exaggerating if I say that’s what the games of dating feel like? If you are a person I love and I have ruined your life recently about this, please don’t answer. 

I feel like your acknowledgement of needing to protect oneself emotionally and forgetting your own rules are completely at odds with the rest of your situation. Does anyone really have the tools to protect oneself emotionally when you are in any kind of situation that is making you feel vulnerable emotionally? Surely that is the whole point of it, the danger and excitement of it all? No cognitive dissonance is greater than the one in which you tell yourself repeatedly that you will not feel some kind of way, that you will not put your heart on the line, that you will protect yourself emotionally, and the moment you realise, a couple of days or weeks or months after the fact, that everything is tender and a little bruised and despite your best efforts you are exactly where you feared you would be. I don’t think that’s your fault, by the way – just that perhaps you can cut yourself some slack for falling. Accidents happen.

Anyway, the game: did you ever double text? Did you track how many times you set a date versus the times when he did? Did you withhold jokes to not seem like a nerd or compliments to not seem like a simp? Or, somehow, did you find a way out of all of this? Those questions are just a few of the many ones I have in my arsenal, in my rulebook for this silly game I hate playing and can’t stop. But that’s the thing: it’s my rulebook and I have absolutely no idea if anyone else is using the same one. 

I think the reason we, or at least I, play rules and games is more a question of trying to complete the game in order to figure out how the other person functions. You don’t know them well enough to ask but you’re trying so hard to impress them and just know what they think and want without making an effort, so you play all these games in your head, hoping if you try this door with this key it’ll unlock something that takes you up to the next level and praying that you don’t rush too quickly into that pathway otherwise the bricks beneath your feet will crumble to dust. It’s about just trying so hard to be polite and to fit in with their world, with their thing, which, at first, seems like another planet. It would be mortifying to ask for a map. 

The problem, then, with finding yourself in such unknown territory is that you’ve come prepared with your own little rulebook and survival guide but there is no way of knowing if any of this works in this new place. Whether this other person is playing by the rules. Whether they’re even playing the same game. Even if and when they claim they’re not trying to appear a certain way (that seemingly perfect and rare moment of truth before the time where you know each other well enough to have to tell it all the time) they’re surely working off some specific set of circumstances, right? And why would they let you in on the secret? And however many different people you date in however many different situations, everyone is coming to it with their own reasoning which makes them play the game in their own way, with their own rules every time. 

The thing about actual real-life games is that there’s always someone who gets lucky. There will be someone who will beat you at Boggle on their first go despite you having painstakingly got better at it over the last 15 years. And, crucially, they won’t care. They might feel smug for a second but that hand-wringing and overthinking and calculating won’t even be a consideration for them. So why do we keep playing? I wish I could tell you there’s a better feeling than winning the game – however fleeting that thrill is – but I haven’t found it. And surely the whole point of playing anything is that, to an extent, it’s supposed to be fun, right? 

But the other kind of playing, playing hard to get, might be deemed a necessity to some extent because of how conscientious you want to be about the other person. Yes you want to be direct and yes you want them to like you for you, but might there also be an element of you thinking this is the best thing to do in order, to, well, be polite? I think there’s that, but there is another noun that starts with the letter P that I’ve made it this far without mentioning which, I fear, could be at the heart of all of this: Pride. 

If Beth Harmon taught me anything it was to learn when to Stop Playing The Game. Like here. Above. She should have stopped playing. Obviously.

In The Queen’s Gambit, chess prodigy Beth Harmon is asked why she is so obsessed with the game. Hers is a very literal one, one for which she sacrifices everything else in the name of being the best in the world. Explaining why she keeps going, she says: “I feel safe in it. I can control it, I can dominate it. And it’s predictable. So if I get hurt, I only have myself to blame.” When you started feeling some kind of way about this boy, did you feel like you could control it? What was the moment in which you stopped feeling safe in it? Maybe this is the emotional protection you mentioned – the games across every kind of message and the days in between dates as a means of insulation for what might happens next. But god, didn’t you feel so proud when he ate right out of the palm of your hand? And if you fuck up the game and text too soon or too late, that way it’s only your fault for playing the game wrong, right?

I mean, I really don’t hope that’s right. I’ve said it before and I’ll say it again – all my friends who are in long, happy, sturdy relationships say that the games are pointless and exhausting and when you find the right person it will not feel like a game, it’ll just be easy. I hope they are right, but I also don’t want to disregard anyone (read: the game player) who, for whatever reason, is figuring out their own rules right now as well. 

I’ve been thinking about a few different Olivia Rodrigo lyrics recently – because I am nothing if not a 17-year-old claiming to be “25” or whatever – and while, obviously, all of ‘1 step forward, 3 steps back’ speaks to all of this headache of trying to anticipate another person’s arbitrary decisions (“And maybe in some masochistic way / I kinda find it all exciting” which then gives way to a “And I’d leave you, but the roller coaster is all I’ve ever had”)  there is just one line on ‘enough for you’ which reassures me that, one day, there will be a happy ending to the game. 

She spends the whole song telling us how hard she tried to impress this boy (“stupid, emotional, obsessive little me”) by learning all his favourite songs, remembering how he takes his coffee, wearing more makeup. He told her that she was never satisfied and, well, clearly told her nothing else that would stop her playing these games. But eventually in the song she realises that this game and this exhaustion isn’t the last one she’ll ever play and that one day, it’ll all be worthwhile. “Someday I’ll be everything to somebody else,” she starts, in a desperately gentle lilt that holds none of the anger or resentment or impatience that I know I’ve felt too often when the game isn’t going my way. 

“They’ll think that I’m so exciting / And you’ll be the one who’s crying,” she goes on. It’s that line there that gets me – the fact that out there somewhere might be someone who could be blissfully unaware of all the hoops I’ve had to jump through, of all the crying I’ve done about someone who probably wasn’t even aware that I tried every single locked door and bonus challenge and magic trick to find a way to get out of there and just get them to see me. Following the rules can lead to success, sometimes. Sometimes, being a chess person can pay off. But, as I have been stubbornly and opaquely trying to say throughout this whole letter, playing a game should be fun. Dating should be fun.

There are so many things in this world that can and will hurt you without flinching – all I can recommend, and try to prescribe to myself as well, is to hold onto this whole mishegas for the tiny bursts of joy its inherent silliness unlocks. The good thing about games? They are constructions and it is ridiculous, and, crucially, you are the one deciding your next move, or when you’ve had enough. You do not have to keep playing. But if you do, and even if you lose one – there’s always another sitting pretty, waiting for its turn as soon as you're ready.

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If you’d like to write in to respond to this week’s letter, or to ask questions of your own (please do!), you can email me here.