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My Middle School Heartbreak Playlist



I don’t know the first time I cried over a girl.

I do know the first time I wanted to.

I know that when I was 13, my girlfriend of probably a week broke up with me on AIM.

I know that I spent the rest of my night in the shower, listening to Kanye West’s Bittersweet Poetry, wanting to cry.

I know that, against my wishes, all the droplets sucked down the drain came from the showerhead, not my eyes.


Only a fool would spend precious time trying to identify why they thought the way they did in middle school. Here’s what I came up with. At the time, my two older siblings were in relationships and it was clear to me that high school relationships last forever. Additionally, both Disney Channel and Nickelodeon made grand romantic teenage love seem easily attainable & I believed in Ned Bigby the way an elderly couple in a dark red part of America believes in Joel Osteen.


Whatever the reason, 13-year-old me genuinely wanted to feel the visceral emotions, both good and bad, that come with “love”.


On Smokey Robinson's 1975 album Quiet Storm, he sings about the price of love. His theory is, some ecstasy, is going to cost you roughly, some agony. I don’t think he is saying that being in divisive relationships is the path to love. I like to think he’s referring to the idea that as we age, and naturally come face to face with more moments of pain, we’re more capable to identify what we love.

At 13, my run-ins with pain & raw emotion were rare. This left me with two options. Accept that in time, I would grow and be faced with more opportunities to feel these strong emotions I yearned for. Or I could listen to the same 10 songs on repeat, artificially exposing myself to the pain and pleasure of love. I chose the latter.


Listen on Spotify!



  1. Bittersweet Poetry Kanye West

  2. Don’t Matter Akon

  3. Find Your Love James Massone

  4. Ordinary People Mathai

  5. She’s Always a Woman Billy Joel

  6. I’ll Be There The Jackson 5

  7. Drops of Jupiter Train

  8. Bubbly Colbie Caillat

  9. How to Love Lil Wayne

  10. Whatever You Like T.I.

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