We Ask, You Answer: What’s Been Your Biggest Heartbreak?

$4.3 billion dollars are spent on Valentine’s Day on flowers alone. Though it’s meant to be a day of celebration, some say it’s just the commercialization of love. While I always expect a card on Valentine’s Day from my husband, I often resent how much brands like Tiffany’s and Victoria’s Secret simplify love. The reality is that love is as complex as it is complicated. And today, we want to celebrate the messy parts of love—the ones that can’t be summed up in a Hallmark card, the not-so-great moments, the broken-hearted moments. No matter where you live, how old you are, or who you voted for, most of us have experienced heartbreak. 

When I tried answering the question myself, What’s been my biggest heartbreak? I was surprised that my answer wasn’t immediately my “big breakup.” You know, the type of one that changes you and shapes you into the person you end up becoming—the ‘growing up’ break up.

But the answer that came to mind first, the one that’s brought the biggest heartbreak and true ache, that I’ve tried to mask and silence with just about everything, is my broken relationship with my mom. I long for the bond we used to once have, when falling asleep in her arms made me feel the safest. I yearn for her mothering, no matter how often I try to convince myself that I don’t need it. It would be simply nice to have her to call and cry to about the fact that I haven’t been able to produce a child in two years, another type of heartbreak. I want to tell her about my fears and my doubts. Some days, I think how wonderful it would be to just call and tell her about a good movie I watched. But more than anything, when Mother’s Day rolls around, it would be soothing to know exactly how to celebrate our relationship and my love for her.

That’s the funny thing about heartbreak; it goes far beyond romantic relationships and knights on white horses. Love isn’t always about grand romantic gestures, but instead, about the messy, complicated bits too. And broken hearts are worthy of being acknowledged and celebrated, too. 

What’s been your biggest heartache? A ‘romantic’ loss? Family? Did your best friend break up with you? Comment down below.

LET'S TALK: what's been your biggest heartbreak?



  1. When I got pregnant, was asked to get an abortion, then my boyfriend broke up with me the next day at my doorstep when his car was still running. I lost ten pounds in two weeks. I was heartbroken and so hurt. In the end, I realized he did me a favor by weeding his disgusting self out of my life. Every heartbreak I ever had ended up being a beautiful gift. Sometimes the Universe haze to take the garbage out for us when we aren’t strong enough to do it ourselves.

  2. My biggest heartbreak is losing my best friend. He’s not gone, but our friendship is. We were inseparable in university. We did everything together. I loved him, but never thought of us being together. I don’t know why. He moved to New York and his new girlfriend didn’t want him to talk to me. I didn’t find out til 2 months after he blocked and deleted me from social media, without a word to be said. His friend told me, and we agreed that he’d come around. He hasn’t.
    I still have this chalkboard up in my room that he built for me while he was working for a furniture design company in Brooklyn. On the back it says Forever. It’s one of those pieces that I can’t take down, but can’t leave up, since it makes me think of him every time I look at it.
    It’s been 2 years since we spoke, and yet he still enters my dreams. I just hope to stop dreaming about it.

    1. Losing friends that were like family is so incredibly hard. There are a couple of articles about this on our site. Hope those help, even if it’s just a little bit. <3

  3. The most difficult heartbreak and biggest mindfuck to comprehend, grieve, and heal came when my boyfriend was killed on Feb 4th, 2014 ….conversely my estranged father of 30 years, traveled long-distance to show up and support me a day following this catastrophic experience. We never know what relationship begins anew when one ends, what manifests, when life isn’t meeting our desires, and how to surrender and trust that each and every experience is informing our evolution.

  4. My father died while I was pregnant with my second son. His suicide was the most heart breaking experience of my life. When my parents split up I got to experience their break up from both sides and feel their pain as they both shared their struggles with me. My mom remarried and my father stayed single. He was there for me as much as he could be. I left for Mexico for a year and while I was away he had a mental breakdown and crippling anxiety. He was hospitalized- I was away. I wasn’t there for him anymore. It refreshes the wound to think that my sons won’t know my father. I still see him in my dreams often and I want to tell him I forgive him. I want to tell him it will be alright. I have to settle for knowing that just because I can’t have our old relationship it doesn’t mean he’s completely gone.

  5. My biggest heartbreak was the realization that my ex-boyfriend wasn’t ready to seek help for his alcoholism. The pain in knowing that I gave all that I had to this relationship, and it wasn’t enough for him to want to change.

    I ultimately left him last year, but I learned more about myself as a person and who I want in a partner. Learned about acceptance about things I cannot change.

  6. My biggest heartbreak was growing up and finding out that my father, the only parent who showed me “love”, was not who I thought he was. That he’s actually someone I strongly dislike as a person.

  7. Mine was seeing my ex boyfriend go into depression as his father’s cancer worsened, his father who he hadn’t had a relationship with for 8 years only to come back in his life with the diagnosis. He pushed me away, distanced himself, came back now & then visibly trying to be happy for my sake, but ultimately he ended the relationship because he felt he couldn’t be the person he wanted to be and needed to process and go through it alone.
    I tried the best I could the best I knew how at the time to help and comfort him but it wasn’t enough, I couldn’t make him happy or change the situation.

    Seeing someone you love in so much pain, emotional or physical, and being able to do nothing about it is absolutely heart breaking.

  8. My biggest heartbreak had to have been my first love, who completely shattered me to the point where I was suicidal. We were both recovering addicts, and the only down side to getting into a relationship with each other was that there was always a possibility of one of us relapsing. He relapsed in April while we were together. He went missing on the streets of East Hastings (if your from Vancouver you know then how incredibly horrific and sad that area is) he sold his phone and everything he had within 24hrs of being down there for meth. I spent my nights and days searching for him down there. I went into safe injection sights, drug motels. And then I finally found him after a week. He didn’t want help. 1st biggest heart break was having to leave him on the street and walk away from the person I loved so dearly knowing they didn’t want the help and I had zero control. I couldn’t sleep, eat, or talk for weeks. I just waited praying for a phone call from him. This turned into a nasty cycle for a few months, we stayed together through it all. How could I possibly leave him? When he was out there for the 3rd time, I honestly wished he would have just died…because at least I could have closure with that, but not knowing where he was or what was going on was eating me alive. Towards the final relapse before I walked away from this toxic relationship. He had a week sober and things seemed ok. He then began to tell me he had been cheating on me every time he went out on the streets with hookers and prostitutes and had been having unprotected sex with multiple woman. I couldn’t breath. It felt like someone had just stabbed me and I was bleeding out. I didn’t know how to understand that while I was praying every night for him to get better, and for him to just come home he was fucking other woman? Soon after this I formed a horrific eating disorder that I’m now struggling with everyday. I lost 40 pounds. I had to go on lots of medication and seek professional help due to all the trauma. The relationship as a whole was my biggest heartbreak. But I didn’t let it kill me, I healed and surrendered to the pain from it. I accepted what happened. I’m grateful for the lessons I learned with all that pain.

    1. Can’t thank you enough for sharing this. I know someone will read this comment and feel so much less alone knowing someone else has experienced this too. Thank you, thank you! <3

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