11… Things I Learned From Heart Break

RaeAnna Rekemeyer
7 min readNov 15, 2021
I don’t know if I’ll ever walk down an aisle in a white dress, but I’ll wear one and a flower crown any day.

Cuffing season is upon us. If you don’t know what that is: the season people search out a partner for the long or short term to cuddle up with through the cold months and/or celebrate the holidays with; beginning in October and lasting until after Valentine’s Day.

As all the beautiful people in the world are coupling up, I’m reminded of one of the possible and inevitable endings every couple faces: the end. Every. Relationship. Ends. Some with a breakup. Others with death… We call these the lucky ones because they lasted. Either way, every relationship ends and is often partnered with heartbreak. Happy holidays! Let’s talk about pain.

Heartbreak comes in all shapes and no two feel the same. So often heartbreak is equated with romantic relationships, but it doesn’t have to be. I’ve had friendships hurt far more than romantic relationships. Whether romantic, platonic, familial, or other, to love is to open ourselves up to pain. So much so that, for me, love and pain are all but synonyms. Not to detract or overwrite the joy and warmth of love, but those feelings cannot exist in the absence of pain. The two breathe in tandem making one all the more poignant because of the other.

My heart may break, but I won’t stop loving.

Autumn and winter are the seasons where couples, families, and friends come together. In Texas, it’s wedding season. The holidays are looming; families and friends are planning gatherings. It’s a time to be with loved ones. Social media becomes even more inundated with people declaring their affections for one another. These occasions also have a tendency to bring up unresolved issues, hurt feelings, drama, and all things heart aching. There’s love and happiness in there too, I suppose. For me, it has been no different. Well, the declaring my love on social media for a romantic someone is far from likely. I’m speaking to the holiday heart aches. Historically, October has been a consistently traumatic month for me. Some of the worst events of my life happened in October. Some of the biggest heartbreaks too. October wrote scars across my heart, so I’m always happy to say ‘Au revoir, October’ and ‘Привет, Christmas!’

In no uncertain terms, heartbreak is the fucking worst. I’m not talking about breakups, friendship endings, or endings specifically. Breakups are not always painful; some pain does not accompany an ending; and heartbreak can happen when no relationship ever occurred at all. It’s the pain that sits unrelentingly inside my chest. Whatever the reason. Whoever the person. No matter the relationship. Pain is still pain, and it has been my greatest, most consistent teacher.

Over the course of thirty years, I’ve learned a thing or two from my heart breaking, and I expect I’ll learn many more. Some opinions may change, and hopefully I get better and less bitter with time. I remain hopeful.

Life is better with love.
  1. Love Hard; Love Ferociously; Love Resolutely I truly believe in loving with everything I have. Friends, lovers, family. I will give everything I have and everything I am. I have never regretted loving someone fiercely; though it has been painful, I don’t look back with regrets or what ifs. Even as endings loomed, I loved hard even when quitting would be the easier thing to do.
  2. Love Has Boundaries Boundaries are hard for me, but I’m learning love, healthy love, has boundaries. Just because I love ferociously and without limits does not mean it’s a free for all. It took me a long time to know what I would endure and what I will not. I was a doormat for a very, very long time, but I’m finally learning how to stand up for myself. That comes with setting boundaries for myself and for my relationships. I’m still not great at this, but I’m trying, damnit.
  3. Timing Matters I wish this weren’t true. Sometimes you meet the right person at the wrong time. It’s so cliché, and yet it’s true. Timing matters, and sometimes that’s the only reason a relationship needs to crumble.
  4. Set Expectations Take this in any and all ways. Friendship, workships, family, sexual partners, romance, whatever. Expectations are so important. If they’re not established, how the hell is the other person to know what I want and need and expect from them and us. Expectations change with time and growth, so continue to talk about them. Have check-ins. Regular check-ins!
  5. A Breakup Isn’t Failure This one took me a long time to come to terms with. I have a deeply rooted fear of failure. Anything not working out was a failure, a personal failure, all my fault, and no one else’s. I know in my brain this isn’t true; my irrational brain has not caught up. Breakups-romantic, familial, platonic-are not failures. Sometimes things just don’t work, and that’s okay. People are not always compatible, and that does not mean either one is wrong or problematic or “crazy.” It just means people are different. The failure is in not trying at all.
  6. Radical Honesty I’m not a relationship expert, obviously. I’m sitting here in my office absolutely single at thirty, but I have had incredibly successful relationships and breakups. People ask me for relationship advice-I don’t know why either. I always say: Communicate all the time about everything. There is no such thing as too much honesty. In my relationships, I practice radical honesty, which is why I’m so close with all my exes. We never had secrets. There was nothing to hide, so when an ending came, there wasn’t anything to be angry about. No dark secret that tore us apart. The problems were on the surface. They’d been talked about for a long time. We tried working through them because we were honest about what we needed and wanted from one another. We gave it our all, but things didn’t work for whatever reason. Lack of love has never been at fault. Radical honesty doesn’t prevent pain or arguments. It may not even prevent a breakup. It does make everything healthier, happier, and so much easier. My life is so much better because I have been honest in my relationships. Even when honesty stings, it saves much bigger pain.
  7. You Will Not Be the Same Person People change us. Every single person in my life has influenced who I am today. Those I have let into the deepest corners of my heart and soul have a larger influence over how I move through the world, which is why I’m choosy! I don’t want to be influenced by crap people. Ideally these very important people make me a better person. Even in heartbreak, I have take aways on how I can do better in the future for myself and in relationship with others. I am not perfect. I never will be, but I am a better person because of all the incredible humans I have loved.
  8. Always Say ‘I Love You’ I have never regretted saying these three words. Sometimes they’re not said back, and that’s okay. I don’t say them with the expectation of hearing it. Love is amazing when it’s reciprocated. It can fucking wound when it’s not, but I will always say I love you to the people I do love because I don’t want them to wonder or not know where they fit in my heart. I say it a lot, but I also show it, but I’m also going to say it. I want the people I love to know without a shadow of a doubt that they are loved.
  9. Fight For Love, But Know When To Leave I have fought so hard for love. Not a regret in sight. I will always fight for love as long as there is a love to be fought for. Sometimes, I’ve fought a lot longer than I maybe should have. There has always been that moment when I knew in my heart it’s time to be done. I can’t tell you when that moment is because it’s different for every person and every relationship. When that feeling settled in, I let go. The pain didn’t necessarily stop, but I learned to stop fighting for something that wasn’t meant to be.
  10. Love Is Not Enough I said this at nineteen. I’ll say it at thirty. Love does not conquer all. Love is not always enough. This is probably an unpopular opinion. Love is enough of a reason to sure try. Many obstacles can be conquered with love, dedication, and hard work from both partners. But there are obstacles that even love cannot surmount. That does not mean the love is any less real or pure. It just means life is ridiculously hard.
  11. Life Goes On I’ve had a breakup where I really wish this weren’t true. I’ve had my heart broken with grief over someone passing or friends leaving my life. The pain doesn’t always get easier. I hate to say it, but sometimes the pain doesn’t go away. I’ve learned to live with those aches like the knee pain I have from my ballet days. Life does go on.

Originally published at https://onthebl.org on November 15, 2021.

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RaeAnna Rekemeyer

Mother of Puppies & Intersectional Feminist | Pants Hater: My dog has anxiety attacks when I wear them. | Busy exploring the dichotomy of femininity.