Anatomy of a breakup

17 Apr 2026 · Read on Substack · 12 · 1

It’s funny to look at your mood tracker and know, without needing to see the date, oh yeah, that was the month I totalled my life.

Not the best September I’ve had

Aaron writes impeccably about How To Not Fail At Breakups:

You’re delivering one singular piece of very bad news, and the news is “this is over.” … Providing Perfect Clarity is a fully secondary goal of the breakup. You get 10,000 points for successfully doing the breakup and perhaps 20 additional points for perfect clarity and if the breakup fails — if you leave the room without mutual common knowledge that you have both broken up — then that is negative ten million points, go directly to jail.

Also: you will feel like a monster.

In my last two breakups, we had dated for around a year. In both there was something that wasn’t there – some crucial chemistry that was missing for me – and I felt that it ultimately wasn’t going to work. So I decided to break things off, though not without a great deal of agonising beforehand.

And so I did the thing, and by Aaron’s definition I for the most part executed it well, if by no means perfectly. But I made it clear what was happening, I didn’t backtrack, I didn’t sit there for an hour talking about it.

10,000 points for me, I guess.


Here’s how it goes.

The week leading up to it, you mentally prepare. You pick a day. Then you sit down and say the words, the little spiel you prepared.

You immediately forget how you expected it to go; it just unfolds the way it does. Perhaps you feel relieved. Perhaps you feel a pang of horror – maybe this was the wrong thing to do, maybe it could have been saved. You might receive some barbed words, or just desperately sad ones. The other party, not having expected this, has made these comments off-the-cuff. Perhaps they won’t even remember them. You will replay them forever.

The week after, things are a bit of a blur. You follow your routine, though without the other person it’s a reminder of the gap they left. You see friends, they console you, it was the right thing to do, it sounds like it wasn’t working, you’ll be okay. You get on with things, keep busy. But beneath the surface, some terrible injury has happened – you just don’t know it yet.

Like people who are exposed to a lethal dose of radiation, you outwardly seem okay. But the damage is there, beneath the surface, waiting to reveal itself. Your DNA has been sliced into a thousand pieces by electrons slamming into it at the speed of light.

In the weeks and months that follow, it will feel like you are dying – organs failing, skin sloughing off. You will know with certainty that this was the wrong thing to have done. You try to remind yourself that it really wasn’t working and it hadn’t been working for some time, perhaps a long time, and there is a good reason why you made this decision, remember? That it’s okay for relationships to end, that you are allowed to end them if they are not working, if some crucial thing is missing or even if they just don’t feel right. That it doesn’t make you a bad person.

And the voice says

but what if it does make you a bad person.

It would be better if they had been cruel, or cheated on you or beaten you up. Those are good reasons to break up with someone. And then there’s it wasn’t really working.

It will feel, not forever but perhaps for a long time, like you’ve blown up your life. And while blowing up your life has much to recommend it, you will find each time you do will be harder than the last, sometimes much harder. You will wonder – how many more of these do I have in me? And no matter how much you tell yourself that you did the right thing, there will always be part of you that thinks: maybe it does make you a bad person. You’ll never find out either way.


I once thought of breakups (both done by me and done to me) as a switching cost, a necessary evil on the way either to finding a relationship that’s going to go the distance, or when circumstances mean you have to leave someone. Or just that it was fun while it lasted – maybe neither of you were promising forever. It’s noble to free each other from something that isn’t working to pursue something that will.

But increasingly I wonder how breaking up (or being broken up with) changes you. Not in a “you are the common denominator of all your failed relationships” way, but more how many times can you sledgehammer yourself in the nuts and live. Perhaps each one hardens you a little more.

The horror is that it’s both. You don’t get to be with someone without risking it ending. Sometimes it ends and it’s fine. Sometimes it ends and you find out soon enough what it cost you. You don’t get to know in advance which it’ll be.