The Worst Heartbreak You Ever Have Can Be the Best Thing That Ever Happened to You
How the relationship that almost destroyed me led me back to myself and inspired me to lead the life I was meant to live
Like nearly everyone else on the planet, I’ve had my heart smashed into a million pieces and then stomped on with steel-toed boots and kicked off a cliff for good measure.
It happens to the best of us and the worst of us, and yet somehow — because we all live in our own unique version of reality — it always seems to come as a shock when that person who we love so much decides they don’t love us back and wants to say goodbye for good.
My biggest heartbreak in life came in 2006 and then again in 2007 and it was delivered by the same person. His name was Tom (actually it wasn’t, but let’s say it was), and even still to this day I think about him sometimes and wish I could talk to him, sometimes even going so far as to romanticize our relationship in my mind.
In reality, it was soul-crushing and sent me (in combination with many other existential factors) into a depression and anxiety spiral that would last for the better part of two years and would leave me broken and exhausted.
I only started to recover when, in late 2009, we collaborated long-distance on a piece of art and I finally understood all the reasons it didn’t work out and let it go while smoking loads of hash and shacking up with a surf instructor in Morocco.
For some reason memories of this relationship and that time in my life came flooding back to me over the last several days as I traveled to my father’s house in Pennsylvania on my way back home to Portugal after a month-long trip to Costa Rica.
The nostalgia started on the flight from San Jose to Newark. The skies were clear, and I had a window seat. As I stared down at the Mississippi River snaking its way across the Midwest, I returned suddenly and completely to a road trip from Kentucky to Missouri I took 15 years ago with Tom, who I thought then was the love of my life.
Tom was — well, is still — a very talented metal sculptor and woodworker. We were delivering a sculpture of his to a gallery in Columbia, Missouri, or maybe we were picking it up. That part I don’t remember.
What I remember was that it was one of the most passionate times I would ever have with someone, and also one of the most troubling. It also marked the last time I would ever see him and, even to this day, it feels like it shouldn’t have been.
Don’t get me wrong; I’m not still in love with Tom. I’m in a thriving and wonderful relationship with an amazing man who I love both simply and deeply in a way that I never thought was possible. After nearly five years, we are so easily together — after an initiation period in which our shadow sides battled one another for dominance — that it just makes perfect sense. I can’t imagine my world without him.
But my relationship with Tom — with whom my partner shares many qualities, though it’s the ones he doesn’t share that probably make us most compatible — was something else entirely.
Star-Crossed and Mismatched
I was 33 years old when I met Tom, and I had lost my mother exactly 11 months before the day we met. It was in September 2005 at a friend’s wedding in Philadelphia — well, actually, the rehearsal dinner the night before the wedding. He was one of two single guys attending the weekend-long affair, both artist friends of the groom from graduate school.
Initially I thought the other friend was more interesting, as he was more outgoing and friendly. However, I have always been a sucker for the strong, silent type — both Tom and my current partner share these qualities. These are the kind of men who don’t say much but when they do, you know they’ve been paying attention, and it’s either astute, or funny — or both.
By the night of the wedding, it was Tom — with his tall, dark and handsome Southern charm — who had my full attention. And I had his, and we spent one of those magical nights together that only happen when you’re young, single and romantic and a little bit drunk on free wedding booze and the love vibes of two people committing themselves to each other for life.
The glow was still there the morning after and, though we lived in separate cities — he in Lexington, Kentucky, and me in San Francisco, California — it seemed like this thing could work.
It didn’t, of course, but in between the beginning and the end — which happened several times before reaching the grand finale in May of 2007 — the ride was exhilarating, intoxicating and, for me, addictive.
Our whirlwind, 20-month romance was filled with late-night emails, long phone calls, romantic proclamations and gestures, visits to each of our respective cities, and romantic encounters in Boston, New York, Philadelphia and even a tiny town in the English midlands.
It really was all so glorious and thrilling — our beautiful, magical hot mess of a relationship — while it lasted. It was all butterflies and passion and deep thoughts and intensity and “you’re the person I’ve been looking for all of my life,” all the time. I still don’t think I’ve ever felt the way I did with anyone else than I did with him, but that’s probably because you’re not supposed to actually feel that way in a healthy, sustainable relationship.
Tom first called our relationship quits seven months into it because he started dating one of his art students at the university where he taught sculpture, but then we reconciled a number of times after that. During that time he was diagnosed with bi-polar disorder, and started on medication, which became a long, drawn-out journey for him that lasted well beyond our time together.
From my perspective, I met Tom when I was in the early stages of grieving not just my mother’s death and coming to terms with the difficult relationship I had with her, but also had just emerged from a codependent relationship with an abusive alcoholic who would die of his disease the same week I spoke to Tom on the phone for the last time.
When Tom appeared in my life, he was like a rescue boat after I’ve been lost at sea for months. Sure our connection was genuine and our chemistry was explosive, and I think if we met today we would still have things in common and be attracted to each other.
But looking back, it just was not in any way, shape or form a recipe to embark on a healthy relationship. This is especially true when that person is coming to terms with his own mental illness. In the end it probably was a case of “right person, wrong time,” as they say.
The “Final” Final
When it all finally careened and screeched its way to a halt, I, too, was like a car that had flipped several times and then tumbled into an embankment — as destroyed as I’ve ever been. And I had to dig deep — really deep — down into the well of grief and loss that was a combination of so many things that I didn’t know where it ended and I began, or vice versa.
I had to rebuild myself into someone completely new and face all the years of my own anxiety and depression and existential struggle that had sent me headlong into someone like Tom, and become the person I was meant to become on my own. This required kicking my codependency and love addiction and many other unhealthy patterns for real.
And I did it. I was single for the better part of 10 years after we finally called it 100 percent quits, after he’d twice left me for other women and decided in the end not to come limping back. (Pathetic as it seems now, I would have taken him if he had!) Not long after, I quit my job to become a freelance writer and left New York City, where I’d moved in the middle of our relationship, for a new life on the southwest coast of Portugal alone.
Sure, that move was not easy, and I had a series of encounters with damaged men during those 10 years that demonstrated to me that I was still in no way fit for a real relationship. But in the end the time alone made me learn to love myself and consider myself someone worthy to be loved, something I never felt before.
Because despite all our challenges, I think that’s what really doomed my relationship with Tom from the start. My thoughts of him these past few days inspired me to go back and read some of the emails we exchanged during our relationship. And only now I see what a completely desperate pain in the ass I was! My insecurity about our relationship and in the belief that this incredible human being that I was so desperate to hold onto could actually love me was so clear from that correspondence.
Who wouldn’t want to escape immediately from such intense and pathetic pressure to be loved by someone who didn’t actually think herself worthy of that love? I don’t blame him for running miles in the other direction; in fact, that he didn’t do it right from the start was a clear sign of his own unhealthy mental state at the time.
So in the end, what I still look back on as the most soul-crushing relationship I ever had — and reflect upon a person I still wish I could talk to sometimes about music and art and life because we really did have a genuine connection and many things in common — I realize that it really was the best thing that ever happened to me.
Without losing Tom, I would have never found myself. I would have never hit my bottom and had to climb back to the top by realizing who I really and and what I really want. I would have never sought the help I needed — and ultimately received — for my mental health and now live a life free of chronic depression and anxiety and instead full of gratitude and joy.
I would have never had the courage or freedom to move to Portugal and become a surfer and live in a place where the ocean and the forest are my playground. (I would probably be living landlocked in Kentucky instead, and while it’s a beautiful place, I’m pretty sure it’s not for me.)
And most importantly, I would have never met the real love of my life — ME — and then subsequently my gorgeous and kind life partner. He truly does make all the wonderful things I appreciate in my life that much better, supports me being me more than anyone I’ve ever met, never projects onto me any of his own mental or emotional bullshit, makes me laugh on a regular basis, and is just an all-around beautiful person that makes life not just more bearable, but more joyful and fun.
So here’s to Tom, wherever he may be, and to those of us who have survived heart-pulverizing relationships and not only lived to tale the tale, but realized that we were much better for it. If there is one thing I’ve learned as I approach my 50th birthday, it’s a combination of the resilience of the human spirit and hindsight that demonstrates how far I’ve evolved past my foolish younger self that make getting older totally worth it.