Sing It, Sister: How Pop Music Can Heal a Heartbreak


I didn’t “get” Taylor Swift, really, until I had suffered an overwhelming amount of heartbreak. Last summer, I spent a few weekends in Westerly, Rhode Island, where my fiancé’s friend owned a home. The buzz there over Memorial Day was all about Taylor Swift, who had bought a multimillion-dollar home in Watch Hill, right off the main strip that ran through town. Everyone I heard talking about Taylor Swift seemed to be annoyed at her presence, which was, basically, just as a specter. I never had much of an opinion about her, because, other than the few upbeat songs of hers I’d heard on the radio, I hadn’t devoted much time to her. Then my fiancé broke up with me, and that’s when I listened to “Dear John” for the first time.

I’m not a 19-year-old girl, nor have I ever dated John Mayer, but something resonated with me when I heard Swift’s voice singing those words. Sure, I didn’t leave the relationship feeling like someone had taken advantage of me, which is what the song implies, but the silly connection I had to Taylor Swift — that she lived in the town where I felt that my relationship had started to tear itself apart — was enough of a gateway drug to lead me into what would eventually be the thing that got me through the pain of my romantic disappointment.

When Swift performed another sad breakup song — or really, a sad post-breakup song — at the Grammys last month, her words and her voice hit me hard again. I watched her throw her head back and forth while banging the piano keys, and I felt how numb she looked as she surveyed the crowd after finishing the number. And I thought of a picture of my ex and me that was taken shortly before sunset on the Fourth of July, on the porch of this giant hotel down the street from Swift’s home, where she was hosting a party. We had just walked down to the beach, barely speaking, to gawk at the group of people on her lawn playing volleyball, wondering if the blonde girl in the red dress frolicking with her friends was actually her. I’ll never know, but when I look back at the picture, which was taken after we walked back up to the deck, I can see how exhausted we both were, how we probably both knew that the end was near, even though it would still be weeks before he told me he wasn’t ready to get married, and another few weeks before he suggested I move out of his apartment.

“All Too Well,” the song Swift performed at the Grammys, is about memory: looking back at a relationship weeks — or maybe months, who knows — after it ended. It’s a song about regret, about second-guessing yourself and everything you experienced. “Maybe we got lost in translation, maybe I asked for too much,” she sings. “And maybe this thing was a masterpiece ’til you tore it all up.” Six months after my engagement ended, still so confused and without answers as to what, exactly, happened, I can’t help but listen to the song without feeling my heart reverberate with pangs of pain. It sounds so lame to admit it — it reminds me of when I used to post dramatic song lyrics on my AIM profile in college to express my current feelings or, later, would update my LiveJournal with a song of the day — but the sense of solidarity I suddenly felt with Taylor Swift made me understand what’s so great about her, and what’s so important about songs like “All Too Well.” It rationalized and validated my own torturous emotions as I walked through the slush and the snow to work, rode on crowded subway cars, or sat in front of my computer at the office with my earbuds in, feeling completely alone despite being surrounded by people. I wasn’t alone, because there were other people who were singing about how badly they felt, just like I did. I felt, as Swift sang, “like a crumpled up piece of paper,” discarded and left behind.

I wouldn’t say that I listened exclusively to sad songs, though I did pretty much only listen to songs sung by women. There wasn’t much I could relate to in music recorded by men, and I couldn’t find any movies, save for maybe Eternal Sunshine of the Spotless Mind, that focused on heartbreak from a man’s perspective. (I have not watched that in the last six months. I’m not ready for it.) And while much of the music I listened to was, in fact, written by men — songs like “One More Bell to Answer” or “Whoever You Are, I Love You” — what was important was that the voice singing the songs came from someone like Dionne Warwick, rather than, god forbid, Burt Bacharach.

There were enough songs to fill up a Spotify playlist, as it turned out. I called it “Sing It, Sister.” And there was one for every emotional situation. If I were particularly angry, I’d double-click on “Get Gone” by Fiona Apple or PJ Harvey’s “Rid of Me,” the latter hitting the obsessive end of the feelings spectrum. If I were suddenly more hopeful, it’d be Diana Ross’ “Remember Me.” (“Remember me as a sound of laughter,” she sings. “Remember me as a good thing.”) Desperation came in the form of Emmylou Harris, who sang, “I would walk all the way from Boulder to Birmingham / If I thought I could see, I could see your face.” Then there were the times when I felt absolutely lower than low, as if life couldn’t possibly get worse and would surely never get any better (even though good sense told me, with time, I would be OK). On those days, it was Jewel’s “Foolish Games,” which is so ridiculously depressing that I would immediately snap out of my funk and laugh at my own melodrama.

And thank god for show tunes, like “What Did I Have That I Don’t Have” from On a Clear Day You Can See Forever, which is sung by a woman who discovers that the man she’s in love with doesn’t love her, but rather the woman she was in a past life. That was the variety of melodrama I was desperate to experience, and the song encapsulates it all in what is the greatest portrait of how love can be lost simply through a combination of time and those little evolutions that we all go through — even those not of our own volition. “Where can I go to repair all the wear and the tear,” Barbara Harris sings, “’til I’m once again the previous me?”

Most of the time, though, the songs I picked helped me understand how to feel. Liz Phair seemed to allow me to accept my anger with her lo-fi “Ant in Alaska,” singing in her perfectly deployed monotone, “I look at my life and I know you’ve forgotten / The promise you made to me, I think that’s rotten.” ABBA’s Agnetha Fältskog expressed how random and serendipitous a connection between two people can be in “The Winner Takes It All,” singing, “The gods may throw the dice, their minds as cold as ice / And someone way down here loses someone dear.” Neko Case gave me permission to imagine I was anyone other than myself when she sang, “I wanted so badly not to be me / I saw my shadow looking lost, checking its pockets for some lost receipt.”

The songs started to define my grief. I sang Fleetwood Mac’s “Silver Springs” at karaoke three times in two days. A friend of mine, a cabaret singer, stared right at me in the audience when she sang a cover of Michel Legrand’s “I Will Wait for You.” I drunkenly danced with my friends at a party to Robyn’s “Dancing on My Own.” At the reception following a wedding, a friend came up and asked me how I was doing. I said something like, “Miserable, thank you,” and she replied, “I figured. I got an email the other day from Spotify that said, ‘Tyler Coates has been listening to a lot of Joni Mitchell this week.’”

The thing about going through a breakup is that it’s exactly that: something you have to go through. It’s not a clean break. It’s like I dropped a glass full of red wine on the floor: I had to pick up the shards of glass first before wiping up the wine. I still find the stains in surprising places, and occasionally I feel the little slivers of glass poking up from between the floorboards. It’s through these songs that I came to realize that what I was experiencing was common and natural, almost inevitable, and it was the words these singers sang that allowed me to come up with my own metaphor for my pain. I’m a piece of broken glass, a collection of shards that splintered off when a full glass of wine shattered.