How To Get Your Heart Broken By A Boy For The First Time

Start to worry. He used to do things like bring you a cup of water without asking and rub your back but now he won’t even bring you soup if you’re sick. This is how you know he’s falling out of love with you.

Become frantic and confused. How can you become the person he still loved two weeks ago? Begin to wear the clothes he has said he liked the most on you. Wear his favorite t-shirt, his favorite pair of underwear—things that you know he adores.  He reacts indifferently to your efforts. Your spirit is crushed and you change into sweats when you get home.

Sex is mechanical and loveless. Tell him that you’re tired of screwing and that you want him to make love to you. He makes love to you after school one day and it’s so intense that you almost cry. Afterwards, you’ll know it’s over completely.

He breaks up with you the next day in a café near school.  Start crying and stare at your croissant. Ask him to cry so you can know that he cared about you but he can’t or he won’t. Call him a piece of trash but then want to give him a hug. It’s all very devastating.

Call your friends. They come running to you and share their stories of heartbreak. They try to get you to eat ice cream and watch a romantic comedy but be like, “No thanks, bye.” You grieve best while on your bedroom floor listening to Mazzy Star.

Become insane. Think of transferring schools and entering independent study. Think of going to boarding school in Iowa.  You wish you had the money to just fly away somewhere but you don’t so here you are.

Your thoughts and reactions will scare you and you will have no idea you could be this crazy. Feel betrayed by your mind and wonder how this insanity ever lived inside of you, how these irrational behaviors could’ve been dormant until you got your heart broken for the first time. Now they’ve shown up as if to say, “Oh hey! You thought you were normal and well-adjusted? J/K! Heartbreak: 1. You: 0.”

Become obsessed with your ex-boyfriend and talk about him incessantly like it’s a nervous tic. By mentioning him at least a few times a day, he still exists and your relationship still happened. When you’re with your friends and you see a blue sky, say to them, “My ex-boyfriend used to love blue skies.” You know you sound nuts but you can’t help it. You are sick, you are not well. YOU HAVE A DISEASE.

Hate your ex-boyfriend. Die from happiness if he ever took you back.

Getting over him is a slower process than you imagined. As time goes by, his name starts to mean less and less to you. You figure this is progress.

There’s no heartbreak quite like when you’re seventeen and you’ve realized someone could love you and then not love you. Just like that. No more love for you.

Wonder if it will ever hurt this bad again. Realize that it does but in more subtle ways. Heartbreak becomes a more controlled insanity in your twenties, a manageable illness.

Sometimes you almost miss the way it felt to get your heart broken for the first time by a boy. But not really. Not really at all. TC mark

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Ryan O'Connell

I'm a brat.


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  • Eliza

    Beautiful. I love this.

  • Moushi

    “being gay is gay: new works from Ryan o'connell” Harper Collins 2011

  • Kev

    This can happen at 30, too. Ugh… (good job, Ryan :).

  • Dhan Michellot

    It reminds me one of the Regina Spektor songs who says;

    “This is how it works
    You're young until you're not
    You love until you don't
    You try until you can't
    You laugh until you cry
    You cry until you laugh
    And everyone must breathe
    Until their dying breath

    No, this is how it works
    You peer inside yourself
    You take the things you like
    And try to love the things you took
    And then you take that love you made
    And stick it into some
    Someone else's heart
    Pumping someone else's blood
    And walking arm in arm
    You hope it don't get harmed
    But even if it does
    You'll just do it all again…”

    Which hurts, but it's true!

  • bailey

    particularly paragraph 6

  • Jane

    You are brilliant with every single written word. I am a fan of you!

  • Noah Tourjee

    Haha, the joke is about getting your heart broken by a BOY though, right? Either that or you're a girl. Right?

    • Guest

      awkward… dumbshit

      •!/evabulgakova Eva Bulgakova

        i think it’s more the latter than the former, really. 

    • Guest

      …what is your problem, exactly?

  • a polar bear

    ryan, date me <3

    • a polar bear

      i will never break your heart. i will let you break my heart.

      • Ryan O'Connell

        Sounds good, polar bear!

  • Elizabeth Greenwood

    I. Love. This.

  • Teeesa

    This is the most spot on thing I have ever read.

  • Karen Chen

    Heartbreak: 1. You: 0


    so… what if it isn’t more manageable in your twenties?

  • SusanDerkins

    This just happened to me for the first time and I’m 28 years old. I guess I just got lucky. But now I feel really bad about all the times I was on the other end. 

  • Miss Jamaica

    Read the title and thought it would be another Stephanie Georgopulos..

  • brideshead

    I think I tore up

  • Sophia

    oh my gosh you actually just narrated my life.
    that’s uncanny.
    ryan mcconnell, how do you understand so, so well

    • Creg

      Ryan o’connell

      • Sophia

        right. i’ve been reading TC for a year. i’m dumb

  • holly

    happened to me for the first time at 27, it is a disease the first time no matter the age.

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