Hello breaking up, you’re hard to do.

Okay admittedly the song is about the dumpee not the dumper, wassailing about the heartache that he/she has on the proposed break up. But the title still rings true for the dumper.

Now I have both been dumped and been the dumpee on numerous occasions. There have really only been  a couple of times that I’ve had a relationship that sorta just ended, but no distinct “break-up” talk was ever entered into (both involved one party moving). Those break-ups were awesome. No guilt. No tears. No uncomfortable conversations. No awkward division of property. Oh if only all break-up were so simple.

But life, being life and consistently wanting to kick us in the nadgers, doesn’t always work like this. So just to provide everyone with an overview of exactly how I came to view break-ups like this, please see below for my life story in break-up form.

12 years old – Natalie (or was it Kimiko?) – asked me to be her boyfriend at the end of year 6. For a glorious five minutes I was over the moon. Then I got dumped for Tony Something  (it’s been nearly 21 years! you can’t me expect to remember everyone names)… the bad boy of the year and also the jock of the school


15 years old – Lenka – the first official girlfriend. I was not interested, but she was friends with my friends and was basically peer pressured into that relationship. I ended it after 3 months.

17 years old – Elizabeth – two years older than me and a dancer. Frankly she was quite pretty. However very, very tall. Whereas I am very very short. I ended it after 9 months after much teasing from friends.

18 – 19 years old – Mei – a great girl, but we were not compatible. I ended it. We became friends for a while, then during this “friendship” she started introducing me as her “boyfriend”. Ended the friendship quickly after that.


22 – 26 years old – The Big Ex – longest relationship ever. But was not ready to get serious. I ended up cheating on her with a friend. I broke it off. Got back together. She broke it off. Got back together. She broke it off. I chased her across Europe (no really I did… it’s basically the reason why I have so much debt). It did not work out as I hoped.

27 years old – the Doctor – I was a mess. I’m not even sure why in the world she was attracted to me. Maybe it was something about her being a doctor and wanting to “save” me. No idea. Clinically depressed because of previous relationship breakdown. Moody. Jobless. She had to move interstate for work after 6 months.

28-29 years old – The Blond – Beautiful, intelligent, sexy, funny. But we we’re plainly incompatible with the exception of the hot sex. Managed 9 months, and then she ended it.

29 – 30 years old – The Wife – yes I will admit it. I had a relationship with a married woman. I’m not proud of it, but it happened. I had to move for work, The relationship again tapered out.

31 years old – the Crazy – seriously this girl was nuts. I mean wow. I don’t think I was even attracted to her. I just got really drunk one night and did not want to admit I was slipping back to my “Slut Years”. Lasted one month and she had to move.  

As you can see, I’m usually the dumper. I have really only experienced being the dumpee a couple of times. But I’ve found as I’ve gotten older, that it’s much easier to take. Admittedly the first time (with the Big Ex) it was for real, it hit me harder than anything I’ve ever known. And with the Blond was tough but looking back not that bad.

But I have not found the same kind of lessening in difficulty when you’re in the role of the dumper.

It’s still REALLY REALLY hard for me.

I will question my motivations.

Why am I dumping this one? Am I just bored? Does that say something about me as a person? Should I not be bored? This is a great person! Why do they annoy me? Am I not built for relationships? Am I a bastard because I don’t really have a valid reason for ending a relationship other than I don’t want to be in that specific relationship? I wonder how much that suit costs? Seriously this is a great girl, what is wrong with me? And so on and so forth.

So how does one end a relationship?

Do you go for the tried and true method of cliche-ing the other person to death (it’s not you it’s me etc etc)

Do you go for straightforwardness (I think we should break up. Reasons outlined in the page 3,6,9, and 13 of the document provided).

Do you go for the “acting like a douche until he/she breaks up with you” method.

Do you go for the cowardly asshole route by breaking up via text/letter/phone?

Do you go for the disappearing trick? Where you simply cease to exist in the same universe as the dumpee?

Or do you have something else you do?

Riddle me that readers.


8 responses to “Hello breaking up, you’re hard to do.

  1. I’d hate to say this was entertaining, but it was. Sorry I can’t offer any real advice, as I havent been involved in any serious/semi serious relationship yet, so I havent had the grand opportunity to dump/be dumped. Though I’d say I would follow the “do onto others as you’d like to be done onto you” advice. And I’d prefer if we skip all the formalities and get to the whens and whys. “It’s not you, it’s me” is nice, but it doesn’t answer the question of why are we breaking up. Those are my unrequested 2c!

    • But I like the 2c! How about we have a standing agreement everytime I post I am requesting your 2c? 😛 I went for the honesty route. Everyone’s right, you want to treat the person exactly the way you would want.

  2. Most people do the “acting like a douche until…” or at least I have. When I flat-out suggested breaking up and he didn’t like that idea, I proposed that we at least both see other people also and he reluctantly agreed, saying that was fine if I wanted it, but he wasn’t personally going to do that (how do you think that worked out?) Yes, it worked out about as well as you could guess – at one point he yelled at me to get out of his car. I don’t remember the rest.

    • Yeah, I’ve been guilty of the “acting like a douche” trick a couple of times. But those with were short-term relationships (3 months or less) where while it’s still not excusable, it might be construed as still an option.

  3. My ex took the act-like-a-douche until I broke up with him route.. except whenever I tried he would start crying and claim he couldn’t live without me. Found out that for 1 of our 4 years together, he had another girlfriend. They’re still dating. They celebrated their 1 year only 6 months after him and I stopped seeing each other. Awkward.

    I would have really, really, really appreciated a straightforward break-up. Really.

  4. * Keep it simple.
    * Keep it short.
    * Leave no “maybes.”
    * Tell her in person.
    * Stay calm.

    And most of all be kind. Then the person can get over you with slightly less heartache. Do NOT give fake reasons or promises to be friends, that’s just a bunch of B.S.

    • *Check
      *Ummm… kinda check
      But I don’t agree with the friends thing. I am more than willing to be friends with an ex, it’s just that when I start dating someone else they start to not wanting to be friends with me. Okay I know its slightly weird, I’m not saying that we double date or anything, or even that they have to like the new gf, just hang out on occasion… or is that actually weird?

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