
Taylor Swift announced her engagement to NFL star Travis Kelce on Instagram this week. While I am so, so excited for her, I can’t help but feel a pang of sadness over the fact that her music will probably never have the same soul-wrenching creative depth that came from the version of her strapped into an emotional rollercoaster. There is a bank of energy that gets tapped by being so broken-hearted you have to do something. The energy you harness can create masterpieces, build businesses, set your life on a new trajectory. It’s why we have so many eras from Taylor. Each heartbreak breeds reinvention. It’s a drug that hits you hard and fast, and also wears you out. I’m happy for Taylor that she can finally have some peace and contentment, but I am mourning for us fans of her saddest, most heart-wrenching work. Thank god we have a huge catalogue to access still.
There is a rawness to Taylor’s work from the times where she was likely at her lowest emotionally. Each heartbreak brought us along on the highs and lows of the aftermath. Even her earlier work, like White Horse, Dear John, and of course the infamous All Too Well have held up over time because of how honest the emotion feels. Dear John came out when I was in high school, but You paint me a blue sky / Then go back and turn it to rain / And I lived in your chess game / But you change the rules every day feels just as relatable today. You would never know that an 19-year-old wrote that- and that, in my opinion, is the power behind heartbreak. It’s universal, evergreen, a tragic club that nobody really wants to be in, but that everyone should be a part of. You are missing out if you haven’t experienced it.
I wrote this piece before Taylor’s engagement announcement, and honestly, I wasn’t sure if I was going to share it ever, let alone this soon. But after my knee-jerk reaction to her engagement was a mix of happiness for her and sadness for the loss of that intoxicating, unstable energy, it felt like serendipity that this was already patiently waiting in my drafts.
I added the Taylor songs and title after the fact, but everything else is untouched. Taylor’s sad-girl music was pivotal to my own emotional rollercoaster breakup, and I think she is the perfect example of the incredible creativity, energy and reincarnation that can come from the depths of romantic sadness.
I knew it was coming before it happened. I was heading into a 5-hour stats exam when I was hit with the worst text you can get from your long-term, and now long-distance, boyfriend: “Jules, I think we should talk. Call me later.” Oh, god. That was the beginning of the slow, painful and dramatic death of the 4-year relationship that had been so pivotal to my early adulthood. I was 21 and so heartbroken I barely left my apartment for days.
This was one of those breakups that felt like it never ended. I would drunk call him, thinking maybe I could trick both of us into forgetting we had broken up. He would drunk call me, another girl leaving his room in the background. It was psychological torture for months on end, it was horrible, and I think everyone should experience it.
Not because I am sadistic, but because there is a romanticism to being so young and so in love and so heartbroken that you feel like you just might die. It’s such a strong emotion that in bringing you to the edge, it has the opposite effect of making you painfully aware of how alive you really are. The breadth of emotions that you feel at 21 when life as you’d envisioned it is crumbling around you is almost unfathomable to 30-year-old me. It’s also intoxicating. It’s a drug I never want to experience again, but I’m so glad I got to feel it.
In the early days of the breakup, I went through many waves of the standard sadness/denial cycle. We’re just on a break while he’s across the world in a different country. Things will be different when he comes back home. Then: what will I do now? I couldn’t envision myself with anyone else. Nobody is ever going to love me in the same way as he does, I just know it. Why was this happening? I did everything right. Then I would go right back to denial. I spent a lot of this time harnessing that energy into a sketchbook, drawing whatever came to mind- both things that made the feelings intensify, but also things that kept my brain busy enough to not think about it for a while. They weren’t good, but they were an outlet for the energy that I didn’t know what to do with.
After a couple of months, the sadness/denial cycle broke, and anger came in. The post-breakup anger is amazing fuel to whatever fire you put it towards. I decided to get HOT. I worked out regularly, bought slutty little bar clothes, and spent my evenings honing my flirting skills. I also decided to be petty- I stayed in touch with his friends, so that my name would continue to cross his path and maybe he would cave and reach out to me. Did you hear that Julie is in Toronto this summer? I saw her at the Wild Rivers concert the other day, she’s still so fun. Man, you really fumbled that. I could build a company from the ground up fuelled solely by the energy that comes from being angry and petty. Hell hath no fury like a woman scorned. True that. He did cave and call me, by the way. Unfortunately, I caved too.
I moved to Woodstock, Ontario three months after our breakup for an internship, and the true sadness stage of grief really sunk in. My intern workload was not enough to keep me distracted, and my friends were all in Toronto and Waterloo. I got really good at Excel, and taught myself to code. I was making automated worksheets and dashboards for anyone and everyone during that internship. Excel formulas and VBA were puzzles my brain could actually solve. They made me feel like I had control over something, that if I just sat with a problem long enough, I could work it out and find a solution. That there was always a simple, logical solution to a problem. Unfortunately, the same logic didn’t really apply to heartbreak. To face this reality, I spent a lot of time driving around aimlessly listening to really, really sad music.
I discovered some great music in this time- Better Man by Little Big Town (written by Taylor Swift, I found out later) was on repeat. My breakup playlist was filled with Adele, Ed Sheeran, and lots of country, but I also loved LEON, The Ballroom Thieves, Blind Pilot. Wild Rivers had a special place in my heart as a band that we used to listen to together live at the Brooklyn (RIP), back when they were just getting their start. I was starved for the most depressing, heart-wrenching songs I could get my hands on. I wanted to feel all of the sadness as strongly as I possibly could. Maybe if I felt it all really passionately, it would go away sooner. It didn’t, but misery does love company, and I was comforted by the artists that had felt exactly the same way I did in that moment.
When those songs come up on my Spotify, I am instantly transported back to 2017, behind the wheel of my mom’s SUV, scream-singing and mourning the loss of what I thought my life was going to be like. My whole being was broken down and getting rebuilt from the studs. It was raw, and hard, but also so, so freeing. Who am I now, without you? Who do I want to be? What do I want to do that I was never able to, with you? The world was suddenly wide open again.

The next two years were a blur of graduating from my master’s, moving to Toronto, and starting a terrible, soul-killing job. My ex was a blip on my radar every so often when our now mutual friend groups would collide. It gave me a sick kind of pleasure every time I heard he couldn’t keep a girlfriend. I felt like I had finally won. Everything else in my life was kind of shit, but at least I had my pride.
On the eve of my 24th birthday, I went to one of our mutual friends’ places. I didn’t know he was going to be there, and I didn’t have the upper hand anymore. My job had been wearing me down for months, I was depressed, and tired, and certainly was not feeling the optimism that the world was my oyster anymore. And there he was: staring at me with the intensity that used to make me weak in the knees. Fuck. We made some small talk. Then, in a pattern that I should have seen coming, he did the emotional equivalent of kicking me while I was down. “You know, I only broke up with you because I thought I could date someone hotter.” I’m sorry? We yelled at each other in our friend’s tiny basement apartment kitchen. I went back to his place, where he had his past week’s worth of work files stacked on the coffee table. I threw them all over the living room. Why are you like this? What did I do for you to treat me this way? What did I do to deserve this? None of this is what I envisioned. I hate my job. I hate you.
This was rock bottom. It was also a pivotal turning point. I started lining up the pieces of my life that I knew I had to change: how and when to quit my job, how to tell my roommates I was moving out, how to finally quit this cycle of feeling so… underwhelmed and annoyed with my own choices. By the summer, I had quit my job, lined up interviews, narrowed down my apartment hunt, and gone on a really, really good first date.
In September, I got a call: “Jules. I need to know. Am I a bad person?” My world stopped. This only happened in movies. I had the perfect opportunity to do what everyone who has ever been broken up with dreams of being able to do. I had to play this right. “…Kind of?”
We met at a bar a week later. He told me that a girl he was seeing had shattered his heart. He wanted to know if it was because he was, inherently, a bad person. I laughed at the irony of him coming to me with this problem. I told him that what he did to me was not great, and that he did kind of suck, but there less malice behind my words than I had originally intended. Here was a broken-hearted man, with nothing left to lose, laying everything out in front of me. He turned to the one person he knew had felt this before- because he had done it himself. He needed to know that this was temporary, that it was a feeling others have felt and gotten through. I told him to listen to some Taylor Swift, and that it will pass. Eventually.
That was six years ago now, and that one really, really good date has turned into six really, really good years. I know, as much as anyone can know, that I will never feel the crushing sadness of a breakup again. All I can do is listen to those sad songs and remember what it felt like to experience so many emotions with so little logic that you feel like you might die.
It’s a kind of freedom that offers a rare opportunity to reinvent yourself, and I think that everyone should experience that at least once in their life. And then go find your happy ending.
see you next thursday,
jules
PS. I made these songs into a playlist you can find here:





This was such a real and vulnerable read, Julie!!
What a fantastic issue Julie!!