How To Not Fail At Breakups

insights from negative 60,000,000 points

[This essay assumes a male breakup-er and female breakup-ee, but would be largely unchanged with genders reversed]

As I discussed, my last long relationship featured literal years of having breakup conversations every few months where I’d go in determined to end it and then, over the course of hours, get talked down. This was incredibly bad for both her and myself. And I think now, with the benefit of hindsight and years of distance, I see the structure of why I kept getting talked down each time.

It was a skill issue.

Here are the rules that I learned, for use if you know intellectually you need to break up with someone, but keep getting talked out of it:

Rule 1: The Only Message You Must Deliver Is “This Is Over”

You’re delivering one singular piece of very bad news, and the news is “this is over.”

You are permitted to provide whatever context you want to provide around this bad news; if she demands context you either don’t have introspective access to or that you don’t feel comfortable giving, you don’t have to give it, because 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.

In my case, she kept asking questions along the lines of “how long have you been feeling this way” and “did you ever want to get married” and “did you know you were going to break up with me the last time we had sex” and I had trouble bringing myself to give the true answers to these because I felt deep in my soul they would destroy her emotionally; but I also felt obligated to give those answers honestly if I had them. So I’d give the terrible answer, and then she would need comforting re the terrible answer, then she’d yell for a bit, and then she would ask more terrible questions which would receive terrible answers until several hours later we were somehow back together (????)

Anyway: writ large, this meant I was doing enormous mental labor for the several hours of being trapped in the conversation, and that led to exhaustion, and the exhaustion would eventually lead to a failed breakup.

Minus ten million points.

Don’t be like me.

Rule 2: The Breakup-er Cannot Be The One To Comfort The Breakup-ee

If you’re in a long relationship then you have a well-established dynamic where you are each others’ go-to person for major disappointments and interpersonal conflicts and if you’re breaking up, then that has to end right now.

Every second of the breakup that you spend comforting the other person with a hug or whatever is a second where you are putting the lie to the actual claim you are making (that claim being “this relationship is over”). You are instead implying to her that this is still ongoing and that you are making a move of some kind.

There’s an even-worse issue: holding someone who is crying and asking “why are you unhappy with me” will make you feel like a monster and will also make you feel that you need to fix it. This impulse-to-fix is the enemy because you can only “fix it,” structurally, by recanting the breakup, which as we discussed is negative ten million points. This gets harder to resist as the conversation continues, which brings us to the next rule:

Rule 3: The Breakup Cannot Take More Than Ten Minutes With You In The Same Room

I think the longer a breakup takes, the more likely it is you’re likely to accidentally take it back. Which sounds fucking insane, but bear with me.

When I’d break up with my ex, she really wanted to understand in detail what exactly had happened and why. A lot of times these attempts at understanding would be in hypotheticals or in asking why I didn’t just propose X or try solution Y to save the relationship. And sometimes the honest answer was “I didn’t think of that” but if that is your answer then suddenly you are now in a negotiation when you wanted this to be over but now you are negotiating on the relationship’s continuation. You have fallen back into the framing where you need the other person’s consent to end the relationship which is not the case.

For the domain of breakups specifically, every state is a one-party consent state.

Anyway, it takes a great deal of discipline and mental fortitude to avoid this dynamic. And you have to avoid it, because if you wanted to save the relationship you would have opened up a problem-solving conversation rather than a this-is-over conversation. You didn’t do that. That’s why you’re here. Your goal is to end the relationship.

(You might say she deserves more than ten minutes of your time. This is probably true. She also deserves to not have you fail at this breakup and the second of these is far more important to her long-term well-being.)

Rule 4: Communicate Only In Writing Afterward

Text, email, whatever. The beautiful thing about writing is that you do it at leisure, in contexts where you aren’t feeling emotionally pressured into giving specific responses.

Any time you’re communicating via voice, either on the phone or in person, is a time when you could, via some accidental combination of words, give her hope that the relationship might be repaired. Your role as Herald Of The End is to give her no hope of reconciliation.

Rule 5: Refer Her To Her Emotional Support Network

While your ex is melting down you cannot be the one to comfort her because of Rule 2.

It feels bad to simply refuse to provide comfort with no further followup. I suggest a slight upgrade: “I cannot talk you through this; please speak to your sister/best friend/mother in order to process this further” explicitly discharges your felt obligation to provide Perfect Clarity and allow your now-ex to process all of her emotions with you specifically, while also providing correct guidance.

Because you can’t help her process all of her emotions. This is a task that will take many months. If you are available for discussion any time she feels like processing her emotions, then you will still be in a relationship at the end of this several-months process.

If You Do It Over The Phone, You Can Have A Friend Keep You Honest

Assuming they’re not violent or otherwise shitty, I think people deserve one— one— breakup attempt in person, out of respect.

If you are talked out of this first breakup attempt, then you are now free to use techniques that are perhaps less traditional, but which are also more effective at the goal of the breakup, such as doing it over the phone.

This has significant advantages: your ex can’t block you from leaving, and you have a kill switch in the form of the “hang up call” button. You can also have a friend standing by listening to the phone call, who will give you the Kill Signal to end the conversation if you’re starting to get sidetracked.

(Also the friend will then be standing by when you’re inevitably like “WHAT HAVE I DONE” and your friend can say “actually previous-you was incredibly certain this has been ruining your life since forever so maybe take a few days before you start second-guessing yourself.” This is a crucial role for friends in a difficult breakup. Also: logistics.)

You Will Structurally Feel Like A Monster

You are taking away your ex’s most critical pillar of her support system at the time when you are delivering her one of the worst-feeling messages anyone can ever receive.

You will feel the impulse to do and say many things in order to not feel like a monster. Don’t. You are the Herald of the End; that is necessarily a monstrous job and the pay is terrible, but it’s yours.

Here’s the silver lining: if you do it correctly, it’s not yours for very long.

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