I Suck At Breaking Up With Girls

I’m really bad at breaking up with girls. No one is good at breaking up with people, but I’m particularly bad at it, because I think I’m doing a good job at it every time. Every time I think I’ve figured it out, that I’ve spent the weekend running recon missions in my head, mapping it out like a raid on Abbottabad. I branch off every possible scenario, prepare for all essential contingencies, turn the page on every looming “what if?”

I lay out my argument with the delicate precision of a trial lawyer, mapping out all the checkpoints that indicated we were going astray. I make a mental path of our relationship and target the point we took a wrong turn, lay out the route as it stands at this moment and where the eventual end point would be (off a cliff, I say, or somewhere hazardous for both of us, while I’m sleeping in the passenger seat and you’re out in the hot desert sun changing the tire. At the very least, unhappy Saturday afternoons at the Target mumbling niceties at each other but failing to capture any of our original excitement).

I explain how unfair it would be for her for us to continue, how my emotions have already withered and dried up and now she’s mining a kicked well at her own expense. I determinately avoid clichés like “it’s not you it’s me” but I say things that turn out to mean the same thing anyway. I go out of my way to offer effusive praise to her, to make her feel like she should not be discouraged by our breakup, to be assured that the world is better for having her in it, that there’s some single guy out there who fits the gears of her brain machinery much better than I ever could (or want to). Every additional second we spend together is therefore pilfering the interest on a bank of lifelong memories of blissful kismet she should be building up with that hypothetical match out in the ether.

I talk too much about her positives: the excitability that I couldn’t match, the appreciation for certain living creatures (cats) that I don’t share, the way her sex drive is admirable even if I did have a headache one too many times when I used to take my pants off at just the flash of a smile (a warning sign, ladies).

I create a layer cake of our relationship and put the break up at the top. It’s not the most important part, because look at all these other thick sweet delicious times we had! Sometimes it just doesn’t work, I say, but the base is still sugary sweet.

Like a diabetic limb, sometimes you just have to cut it off before it gets gangrenous and ugly, offensive to passersby and spreading to the parts of our souls where optimism lives. I rigidly insist to myself that we need to end on good terms; that the bitter flame outs and violent breaks of pop culture are impossible when you have your emotions under check, when you approach a break up with cool rationalism and an understanding that sometimes you can’t force affection. The economic existentialism of sheer rationality.

But here’s the problem: I’m really bad at breaking up with girls because I never really can tell them why I’m doing it. I refuse to niptick, to attack each element of her personality that doesn’t quite mesh with my own, to mudsling a campaign against her personality that would have negative effects in her poll numbers from here on. Maybe what she’s hoping for is a complete breakdown, but what use is that? Why end a good relationship on bad terms by pulling out the individual strands of annoyance that contributed to this mess of incompatibility? The whole point of this thing was to not end on bad terms, and a complete Powerpoint presentation on her flaws seems anathema.

I can’t really pinpoint one exact thing: she’s too intense? Has too many cats? Likes me too much? Doesn’t like me nearly enough? Just doesn’t get it that you can live a low-impact life with little drama and still preach love and tolerance in her daily life?

My venues are always tragically tone deaf too. Twice I’ve done it while using social media deals. Twice. “This relationship is like Groupon,” I heard myself saying in my head, forcing a secret chuckle: “it’s half-off.”

One time, during a bathroom break at a lunch restaurant with the soon to be ex, I absent-mindedly grabbed a handful of free NYC condoms. Later, after we had “the talk,” we sat on a park bench, embracing and sad, when one of them edged out of my pocket, its foil shimmering in the sun. Terrible, record-scratching silence followed. I tried to laugh it off: “it’s the new design! So cool!” “It’s a force of habit whenever I see them!” Humorous deflection can’t undo the real meaning she must have seen: I intend to have sex again soon, and with some girl who is very much not you, and I want to be prepared.

Once I wrote a really long letter to a girl who was about to be broken up with while sitting at the side of the South Carolina marsh (as a buffalo wing festival raged on in the park behind me). And all that was to ultimately disappoint her when she realized the four-page letter contained nothing more than the sentiment, couched in purple prose and a writer’s flare for knocking over emotional checkpoints sentence at a time, “just wasn’t feelin’ it.”

During my breakups, we circle around the issue but I can’t ever accurately verbalize the detonation clause: part of it is due to all my years spent as a writer, which has sapped all communications skills from my mouth and channeled them exclusively into my hands. Once my well-rehearsed argument breaks down at the inevitable question of “but why?” my script for the perfect breakup goes up in flames, and I find myself crouching around this little nut of intuition that refuses to take the shape of words.

Every time I think it’s going to be different, every time I expect it to go over like canceling my T-Mobile service: She: “And why are you leaving us, sir?” Me: “Oh, well it’s just because I got an iPhone for my birthday.” She: “We understand sir. Thank you for your loyalty over these years!”

Every time I expect to have stumbled upon a major revelation in the female mind, thinking I’ve discovered the “exact” phrase or combination of words that add up to “you’re great,” “don’t change,” “this is my fault,” that she wants to hear. When in actuality the fundamental flaw is that there isn’t anything she wants to hear beyond a complete and utter full-reverse from where this conversation started, lunging even farther in the other direction of overt affection to make up for my dalliance in the negative side of the line.

I am, conversely, very good at getting broken up with.

I need it, because I feel like I deserve it after all these terrible breakups I perpetuate. After each time I do the breaking, I see the weight tip onto the other side of the karmic scale and I feel the brutal winds of retributive heartbreak churning somewhere far away. If a relationship is dawdling in the negative zone — that is, the period where I realize there’s an imbalance of emotion, which, in the case of me getting broken up with, means I dig her more than she cares to dig me — I get impatient, want it to get over with already. I’ll force the issue if I have to: if you’re going to break up with me, I’ll say, let’s do the fucking thing, and I’ll get on with my life. Sad, sure, depressed, probably, wounded and made to feel a fool, entirely possible. But the world of young single people in New York City is too big to be wasting my time on someone who doesn’t care.

I absorb a breakup like a hot punch to the neck — jarring, deserved, unfortunate, educational. Don’t stick your neck out and you’ll never get hit like that again.

But I love a good punch every now and then. TC mark

image – Garden State


More From Thought Catalog


    It's so hard to break up with people. Forty different people across the country think I'm still dating them because I can't find the right words.

    • http://www.facebook.com/profile.php?id=1363230138 Michael Koh

      But have you spoken to them? I personally stop talking to people when I decide I'm done. #winning

    • http://twitter.com/nanabuuui Anna B

      champ status.

  • Jackson

    who read this whole thing

    • http://twitter.com/nanabuuui Anna B

      I skimmed <3

    • http://twitter.com/timdonnelly Tim Donnelly



      I did – was I not supposed to?

  • http://shadood.tumblr.com Caroline

    I wholeheartedly agree that writers have verbal communication problems.
    I've gotten to a weird point in my life/career where instead of telling
    stories I make my friends wait until my articles are published.

    • http://twitter.com/timdonnelly Tim Donnelly

      in retrospect, this is probably more of the problem I should have focused on. If I could break up entirely via email or ink-and-paper means, it would go much more smoothly. But I still feel like you owe someone a face-to-face breakup.

  • FvEg

    One time I broke up with someone so horribly that she moved to California. Like, she specifically said “I moved there because it was the furthest place from you where I already had friends.”

  • Clark

    sorry dude, but people need to know why. and logic plays little to no part in one's reaction to a break up so your carefully cratfed arguments are not necessary. just get real and be honest in a nice way. if she's too intense, say “I can't keep up with your intensity.” if she has too many cats, say “i can't see myself living with so many animals.” if she likes you too much say “i'm not in the same place as you emotionally.” there may be tears, there may be begging, it will be ugly. but as long as you do it with compassion the friendship can remain – eventually, once the sadness has worn off and there's some distance from the whole messy ordeal.

  • Teukros

    Your first mistake is in your first paragraph. What makes you think you could ever map out every scenario when you're interacting with another person?

    What defines being good at breaking up with someone? She doesn't need to know why. She doesn't need to be your friend. If you get it done quickly and decisively, with no room for anyone to expect a rebound, then news flash: you're good at breaking up.

    • http://profiles.google.com/mopeyprincess mopey P

      “But if you're honest, and direct,
      And avoid making a flowery emotional speech when you break the news,
      The boy will respect you for your frankness,
      And honestly he'll appreciate the kind of straight forward manner
      In which you told him your decision
      Unless he's a real jerk or a cry baby you'll remain friends”

      • http://twitter.com/timdonnelly Tim Donnelly

        sad that I had to google this. I am a shameful representative of the 90s generation.

      • http://profiles.google.com/mopeyprincess mopey P

        I didn't do a great job of conveying the 90s angst building in his voice.

  • coffeeandinternets

    The worst, worst thing guys tend to do when breaking up with me — throwing the “but I still want to be friends” phrase in at the end. Yeeees I have spent this past week/month/whatever fucking you, just hoping to some day achieve the golden ticket of platonic harmony.

    I have enough friends, douchebags. Just end it with the usual “ex girlfriend issues, don't want anything serious, you remind me of my mother” lines and leave it at that. Don't make me hate you more than I have to.

    Good on you at least for not just doing the “fade out,” and attempting to gracefully end the relationships. That's better than many even offer.


      I want to hear more from Coffee and Internets!

    • dimestorekarma

      is it in fact better to burn out than to fade away?

  • ribcage

    I feel you. I, too, am terrible. Nice piece.

  • SousChefGerard

    Text messaging has made this face to face act both horribly dated and despicably efficient. I'm not the worst.

  • amilena

    I really liked this, because most guys I know would never have the self-awareness to see how bad they are at breakups. But really, any way you slice it, a girl's never going to like getting broken up with unless she's checked out of the relationship as well, which might be why no matter what you say, it never seems like the right way to break up. I've appreciated it most when guys are honest (but not blatantly so, not blunt) and say that they're just not feeling it anymore and they don't want to lead me on and waste my time. Better than the whole “you're so awesome, I just don't have time for a relationship, blah blah” spiel.

    Oh, and never be like “I hope we can remain friends.” 90% of the time (totally made-up statistic) girls will think you're trying to come off as the good guy and let her down gently… And honestly, would you settle for a downgrade from fucking and loving each other? I certainly wouldn't, at least not until all wounds have healed.

    Anyway. Breaking up is tough shit, at least you're making an effort to make it go down smoother.

  • South Carolina Girl

    As the recipient of the long, flowery letter that was written on the perimeter of buffalo wing festival, I can say that the only line I remember from that letter was when you admitted that the letter was mostly cathartic for you. What the fuck?! You really had to leave me with four pages of prose to make *yourself* feel better. Luckily, it turns out we were much better friends than lovers, so I can forgive you for it. But I will agree that you suck at breaking up with girls.

  • http://profiles.google.com/alyssa.mccutcheon Alyssa McCutcheon

    oh my gosh, i haaaaated calling tmobile to cancel my sidekick when i got my iphone. so guilty

  • this is this

    After each time I do the breaking, I see the weight tip onto the other
    side of the karmic scale and I feel the brutal winds of retributive
    heartbreak churning somewhere far away.


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