A Flawed Guide to Heartbreak

October 22, 2014


I used to have a boyfriend. And then we broke up.

After three years, we arrived at the decision that we didn’t want to spend our lives together. It was that simple, and it was that complicated. I will refrain from sharing any further details (until some distant day when they inevitably manifest as essays).

The truth is, I’m notoriously bad at saying good-bye. I can barely part with leftovers or recycle old magazines. Severing ties with people? Don’t get me started…

There’s the denial period, where you bolt awake at 3 AM and suddenly realize they’re gone, followed by weekends that stretch on endlessly. “You’re better off!” everyone swears, and intellectually you agree, but you don’t feel better off. You feel way worse, which is why there’s snot running down your face.

“You didn’t do anything wrong!” friends counsel, like a gaggle of well-meaning defense attorneys. But your righteousness can’t accompany you on Saturday morning coffee runs or bicker needlessly over which Netflix movie to choose. You miss that. You grow nostalgic for the time your partner forgot to put the seat down and you fell into the toilet in the middle of the night. Everything looks bleak.

Since wallowing in a tub of ice cream is only fun for about an hour, here are seven things I’ve learned, including tried-and-true advice from people wiser than me. I hope it may bring you some comfort, too (if and when you need it).


1. Listen to your friends. But don’t ONLY listen to them.
Your friends know you and why you’re amazing. Lean on them. But unless they’re licensed therapists or the Dalai Lama, resist the urge to take their words for gospel. Some friends would have you rebound immediately, while others insist on months of dating detox. Only you know what feels right for you. Seek the advice of a therapist, if it helps, or even the words of a seasoned advice columnist. I’m especially partial to Ask Polly, whose tough-love answer to this question is one of the best things I’ve read (*on the internet, at least).

2. Remember: You are not alone.
Countless people have felt just as bad as you do. Whenever I’m in a funk (and frankly, even when I’m not) I love to turn to the brilliant archives of Modern Love, where there’s an essay to match almost any situation. It’s weirdly comforting to know that smart, sane, kind people have gone through horrible divorces, cheating scandals, and massive relationship anxiety. Not in a misery-loves-company way, but in an inspirational they-came-out-the-other-side-and-so-will-I sort of way.

3. Connect with something bigger.
…and suddenly, the relationship seems small. If you’re spiritual or religious, go to temple or church or synagogue. Find a meditation group. Seek out a feel-good guru. It can be anyone from an energy healer to a masseuse to a yoga teacher to a free online talk, like this one. If reflection feels painful, sign up for a class. The important thing is to connect in a way that makes you feel restored, refreshed, and part of a greater whole.

4. Take two aspirin, feel better in the morning.
The most startling (and useful) discovery of all: Can taking two aspirin actually ease the pain of heartbreak? Turns out the answer is YES. No prescription necessary.

5. Cut yourself some slack.
Forgive yourself for the choices you’ve made and forgive your partner for theirs. Take stock of what you contributed and what you’ve learned. Anger and resentment are unproductive emotions, and the sooner you can own your actions, the faster you’ll be on your way to feeling as good as new. It’s fine to make mistakes. Apparently everyone ignores dating dealbreakers, anyway.

6. Read something.
Namely, this book. I read it over the course of two days and it CHANGED MY LIFE. Sometimes you’re on your way to a breakthrough and something gives you the little push that finally makes it happen. This book did that for me, and I’d highly recommend it.

7. Then go hug something.
Anything but your ex. In the wise words of Oprah, Knower of All Things:

“Romantic love is not the only love worth seeking. I’ve met so many people longing to be in love with somebody, to be rescued from their daily lives and swept into romantic bliss, when all around there are children, neighbors, friends, and strangers also yearning for someone to connect with. Look around and notice—possibility is everywhere.”


One morning you wake up and the sun looks a little brighter. Your leg wanders over to the other side of the bed and instead of missing a presence there, you think “OMG YES I HAVE SPACE.” The world, which had contracted so painfully, feels huge and full of possibilities. And holy crap, they might be even better than before.

There is always tomorrow. Thank goodness for that.

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  • Ah heartbreak, I know this one all too well. I broke up with my boyfriend of 4 years at the beginning of this year, and although it was the right decision it felt like everything was wrong. I then went on to date someone new almost immediately (not intentionally, but you can’t choose when you fall for someone) and he also broke my heart. I’m now on a dating detox and feeling so much better for it. I find travel helps, and a lot of time with friends and, of course, cuddles with animals.

    I wrote something similar recently if you fancy a read: http://www.charlotteswebblog.co.uk/2014/07/how-to-survive-ptone-of-one.html

    Hope you’re feeling OK! xx

  • Oh Caroline, I am sending so many positive vibes your way. This post came in perfect timing for me, I’ll spare details, but just know that reading this is just what I needed at the moment. Surround yourself with goodness. Sending you lots of love.

  • Oh, Caroline, sending you lots of sunny thoughts. (You are such a beautiful writer.)

  • Dear Caroline,
    one day you are going to walk down a street and you’ll see someone vaguely familiar and in that tiny moment when you want to wave to him you realize…. it is the source of this massive heartbreak. And then you’ll just walk on, realizing that you are …. free. The incredible feeling of relief.
    Take care,

  • Oh my, you can’t imagine how much I appreciate this! I turned 30 this summer, and have been with my partner since I was 27. I have been recently grappling with feelings of, I’m not sure I want this person to be the one I spend the rest of my life with. (I feel terrible to even write that.) And then there’s also the: “But I’m 30?!” feelings. 30. Yikes. How did I get so old? Is it harder to date at 30? I don’t know. I certainly have some thinking to do. Thank you for sharing this.

  • I applaud your vulnerability! And I am sending you strength, woman. These kinds of times make us better humans, I swear. I went through a super rough break-up in my 20s and now, some 15 years later (after having been married to another wonderful guy for several years), my ex boyfriend and I are the best of friends. I wrote about the healing here:


    Life unfolds in unexpected ways…
    Sending you good thoughts.

  • Alexandra,

    Another book worth reading is Tiny Beautiful Things, by Cheryl Strayed. Covers anything from heartbreak to miscarriage to high school drama and everything in between – not an exaggeration to say that it changed how I look at just about everything in my life.


  • Caroline,
    So pleased to come across your blog through Joanna. I just stalked you a lil bit and read through some of the archives. 😉 I love your work and thoroughly enjoy your writing style. In regards to the boy stuff… You’re on the right track! I always appreciated taking time for myself after a break up and indulging in lattes and good books. I went through a terrible break up before I met my husband and I just remember feeling so alone. Don’t hesitate to reach out. When my husband and I were dating it was like all the little pieces finally came together… I really felt like all my previous experiences had prepared me to be the right partner for him. Not to mention I became my calmest, happiest and most content self. There is a man who will be your perfect balance (and yet still challenge you) and make you laugh until you pee. Stay encouraged!

  • i clicked on every.single.link recommendation. I broke up with my BF of 5 years in April, jumped immediately into something new, which also ended after a few months and now find myself mourning TWO breakups, while simultaneously trying my very unskilled hand at dating. its… a lot! internet hugs to you, and THANK YOU for sharing.

  • Just found your site, and I love it already. This post is spot-on. I went through a horrible breakup at 25 and it was like my world was ending. Though I’ve found that time is the only thing that really helps. Sending you positive vibes!

  • Great post. I went through my own heartbreak this summer and it’s funny how it can feel so isolating even though almost everyone has been through it at some point.

    I loved this particular This American Life podcast on breakups (339: Break-Up). It’s worth a listen to whether you’re feeling better or not!

  • It might be a small solace for now, but it has helped me in the moment to know that I was being strong and doing the right thing. You’ve done an incredibly brave thing by ending this relationship–other people just give up and stay in it. You are putting yourself first. That’s really beautiful! You know yourself and you know what you want and deserve. And the next relationship will be better because of that. It can be reassuring… albeit it in a small way.

  • Caroline, thanks for sharing your story. I have been there and know what you’re dealing with. If it’s any consolation, I got through it and found much happiness on the other side! In the meantime, maybe this poem will help. It helped me.


  • Hi Caroline, I came to your blog from A Cup of Jo and I adore your writings. This is some wonderful self-healing advice. You seem like such a smart, cool and lovely gal. I’m in NYC too and have been through what you’re going through (haven’t we all) and just want to send you some love from my little corner of Brooklyn, hope it reaches you in yours. xx

  • This is beautifully written and rings true as someone who can relate to your experience all too well. Best of luck!

  • “One morning you wake up and the sun looks a little brighter.”

    For me, progress appeared as the recognition that daily life was now a lighter shade of gray.

    It took a long time to feel like I was living life in color again, but that day came too.

    Stay strong!

  • I am soooooo glad Joanna shared your blog, new favourite blog on my list !!!!

  • Sorry you are going through heartache, I certainly have and can relate. I love your tips. During my last breakup I practiced Tip #1 a lot. I let my friends hug me and encourage me while I cried and talked to a therapist. This too shall pass. Thank you for posting.

  • This is me now and all of these have been milestones for my journey through i. You’re an amazing writer and this is so very relatable!

  • Beautiful post, Caroline. All of your tips are good ones for getting through heartbreak. I found that writing letters I’d never send to people who hurt me helped me find closure. I would thank them for what they taught me and tell them how they hurt me too. I’d write and write and then throw it out, but it’s like your heart thinks you’ve actually had that conversation with them. As a writer, I thought this might help you too. Love from SF.

  • Hi Caroline! I came over to your site from Cup of Jo and just finished reading through your entire blog! I got totally sucked in. You have a really wonderful voice that is so easy to connect to. What a lovely corner of the internet you’ve made.

    When I went through my last break-up, I flew home to Los Angeles and went to Disneyland with my best friend. It suddenly got freezing, so I bought an absolutely huge, hot pink sweater with Minie Mouse on it. In it I felt like even more of a huge loser. Then, in line for Space Mountain, a five year old boy pushed his friend into me, saying “He likes you!! He thinks you’re cute!” I laughed so hard and for the first time in days, because 1. my best friend kept saying “see! SOMEONE likes you!” very loudly and insistently and 2. it was true – someone did like me – my best friend, just as I was. And even if that was that, it felt better being the person I liked being around people who liked me back, rather than subtly changing little things over and over again to earn a love that, in the end, wasn’t worth it.

    I then thought of the last man who I thought had loved the real me in that same way, my high school boyfriend. He’d been trying to call me for months. When I flew back I picked up the next call from him, and after two years we got married.

    You do you girl. You’re an amazing writer and seem pretty awesome – you got this.

    Hugs from the internet,


  • Caroline, I found your blog via Joanna on Cup of Jo like so many others and I’m so happy she decided to include this post of yours. When I read your posts it’s like I’m catching up with a girlfriend and coming from someone who just moved back in with her parents after several years of living with her partner, that is so welcome! I admire that you’ve opened up about such a painful topic but I have no doubt that you will find someone wonderful to spend the rest of your life with. In the meantime- dog cuddles are the best! Hugs from California

  • I found your blog by way of Joanna’s link and I am so floored by your amazing writing! We are so inundated by words and stories but few are so well written. Reading this lifts my day, despite the subject matter! Probably not the intended take away, but here we are!

  • Hi Caroline,

    Like many others, I came to your blog via Joanna. I was instantly impressed and sucked in! You are a beautiful writer with compelling content. I will most definitely be a return visitor to Hello, I’m Flawed.

    I am sorry to hear about your break up. Hope you are feeling OK. As you said: There is always tomorrow. Thank goodness for that.

    Thank goodness indeed.

    Sending positive vibes and virtual hugs your way!

  • Thank you for your perfect timing and for saying all the things I am still struggling to commit to paper/webpage myself.

  • What a beautiful post, you give the most sensible, wonderful advice. Hopefully this will help so many people get over the pain.

  • Anne Roy,

    I am sorry that your relationship did not last. The essence of life is change & initially quite frightening it brings us to good positive change as well as sad, scary changes. Anne

  • Alyssa Czerniak,

    I’m so sorry for your situation, albeit this was back in October but still. It’s ironic, I remember reading this and thinking it was so well written and sounded like such solid advice but at the time I was in a relationship (3 years as well) so I didn’t think to much of it. However, this past week my boyfriend and I ended our relationship and I was drawn back to this page.

    I truly hope things are going better for you know that some time has passed and I want you to know that as another individual who is currently going through this, I can’t thank you enough for posting.

    • I’ve never spilled out my feelings on a blog but theres a first for everything. I’m going through a very confusing breakup right now. We’re so drawn to each other but we know it must end soon as I am possibly heading off to start my life in california and he plans on staying in Florida. I’ve gone through every possible resolution to which may solve our dilemma but I seem to be stuck in this one. Adults laugh when I tell them Im in love at 18 but we’ve been together for three years and have gone through hell and back to be together
      Part of me wants to stay and look at the different options I have here in my state and a part of me wants to move. I don’t know which one is the right choice

  • I know this post is old, but I wanted to thank you, Caroline, because this is truly helping me right now. I’ll be re-reading it over the next few weeks, I’m sure 🙂 thank you, and wishing you happiness

  • Girl. Here sobbing husband walked out after 8 years. thank you thank you thank you.