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The Art of Breaking Up

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Goddess knows, I am no expert at the shitty art of breaking up with people; far from it. But I have a lot of confidence in my own good advice about breaking up that I’m just not amazing at following. Since my social network seems to be brimming these days with recent broken hearts and I’ve been feeling a bit down myself, I figured now was as good a time as any to write a post I’ve been meaning to write for years.

It’s easy and understandable to agonize over the decision to end a relationship, but at the end of the day, I’m pretty convinced that young or old, poly or mono, gay or straight, kinky or vanilla, it mostly just comes down to your answer to three basic questions.

1. Do I like who I am when I’m with this person?

You can rationalize all day about whether you like the person, make excuses for them, and tell yourself that they’re just mentally ill, etc. etc. etc. But take a long hard look at yourself and ask yourself: does this person and my relationship with them make me a better or worse person? Perhaps the answer is “neutral,” in which case, continue on to the next questions. However, generally speaking, unhealthy relationships turn us into the worst versions of ourselves, while good relationships help us manifest the best parts of ourselves.

2. How long has it been since I felt happy/satisfied/fulfilled with this person? How long am I willing to wait to feel that way again?

The most damning answer to this question is, of course, “I have never felt happy with them.” But more commonly, people had a glowing period of New Relationship Energy (NRE) in which to enjoy their relationship, and then settled into something decidedly less glowy that they stayed in hoping to return to their former glory days. Or maybe things were good for a very long time until Something Happened (a child was born, a parent died), and the relationship has just never been the same since. At that point, you kind of have to set a timer for yourself, and try to force yourself to keep to it: “I’ll give this six more months to get a lot better, but then it’s time to go” or “I’ll give this a couple more years with some couples counseling before I throw in the towel.”

It’s also important to distinguish where you are on the scale of dis/satisfaction, which spans from “glowing” (spoiler alert: that’s not usually something that lasts very long for anyone) to “happy” to “fine” to “boring” to “miserable” to “abusive.” If you demand “glowing” all the time, you will never keep a relationship for long; for some situations, “boring” might be good enough, but for most situations, “miserable” and “abusive” probably aren’t. Ironically, mediocre relationships are often harder to leave than “miserable” ones (though usually not harder than “abusive” ones), just because your motivation to get out is lower, and you feel guiltier about leaving.

The calculations for how long to wait here are the result of some complex multiplication involving life entanglements (houses owned, children raised), time together spent in joy, and time together spent in misery vs meh. Be brutally self-aware of your math, plotting out the time you spent together happy (two months? Two years? Two decades?) vs time spent in misery (two months? Two years? Two decades?) vs time spent in “meh” (you get the picture). The most common trajectory I see is people who were happy together for six months who then manage to eke out the next year-and-a-half before finally giving up. 2-3 years is pretty much the well-researched cutoff line for classically defined NRE style affection, so the timeline there is fairly predictable.

3. Would I be happier “alone”?

I’ve put “alone” in quotation marks here because frequently poly people aren’t making a choice to be alone or not, but rather “just” with their other partners vs additionally with this partner. Regardless, the very human temptation here is to ask yourself, “could I get a better relationship than this one?” You’ll never know whether you’ll find another partner, and you may be seeing Potential Competing New Partner over there with the beer goggley gaze of NRE. New Partner looks to be filled with the promise of joy, while Old Partner looks like work. But it’s very hard to know the future of your relationship with someone you haven’t been in one (for long) yet with. one thing you should be able to hopefully calculate with realism is how you’d feel without this person.

Conversely, So. Many. People. Stay. In terrible relationships because they’re convinced that they’ll never find a better partner than this one. But it’s not about finding a better partner or not: it’s about the relative soul rot of being in a crappy relationship vs being without it. Only you can know how unhappy the relationship is making you compared with how unhappy you’d be without it.


There are lots of other considerations that influence whether you should stay or go. These include everything from “we have kids” (which I did mention in the time math) to “my primary loathes this person.” Those factors may all turn out to be much more important for you than any of the ones I have listed here, which are targeted more purely at the relationship in and of itself. If you end up basing your calculations on something other than your own happiness, it’s still at least worthwhile to do so consciously. This can, for example, help you avoid one of the classically stupid poly situations that often arises of “my primary loathes X […because X is actually terrible for me…], but I’m mad at my primary for hating X.” You can get out of that situation by realizing your own damned self that X is terrible for you, irrespective of your partner’s feelings about them. Lots of poly people think they have “jealous partners” when what they actually have are partners who are sick of them dating terrible people. Meanwhile, if you’re basing your decision to stay together on something like supporting your children, for goddess’ sake, try to be good parents together. Whatever devil you choose, do it with your eyes wide open.

I’m going to close this post with some Valentines for my exes. I strongly suspect that some of these emotions will resonate with others, and if they feel painfully familiar to you, maybe that should inform your choices…


It’s amazing how little someone can leave behind when they never intended to stay.


I wish that I could have reflected your best vision of the person you wanted me to be, instead of reflecting your anxieties about the people you were afraid I was.


I worry that the mere fact of loving you made me complicit in the awful things you did to other people.


At least once a week, for years, I still fantasized about having sex with you. I only stopped after you broke my heart again into even smaller pieces of exactly the same shape.


I was always more in love with your kinks than with you.


I wish that our beautiful friendship could have better withstood me falling in love with you.


I don’t get a magical denouement where I get to make everything better. I just have a hole in my life to remind me of the way I failed.


The first time I said I loved you was the last time I ever saw you, and despite the passage of years, I still can’t decide which part of that I regret.


I almost left the scene because I couldn’t tolerate being in it without you.


If I had a chance to be with you again, I would love to be someone I never got to be on the first try: myself.


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