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The Unsent Letters to the Men of My Life

Have you ever written a letter to an old boyfriend, articulating things that were left unsaid, writing for a sense of closure, only to leave it unsent? I’ve done that twice in my life and both times I thought I was completely over my ex. I was happy to finally feel unattached and independent, only to soon hear a song that reminded me of him or to unexpectedly stumble across an old photo of us, causing my heart to drop into my stomach and knots to fill the void.

Alanis Morisette has a song from the late nineties, “Unsent,” where the lyrics are made up of letters to her former boyfriends. Although the song contains personal accounts of Morisette’s relationships, it is very relatable to most women because of the types of men she depicts in her song.

There is the guy she likes but is unavailable; the bad-boy heartbreaker; the “too nice” of a guy she plays games with; the adventurous yet also dangerous; and the one that she learns the most about herself with. We’ve all dated these standard set of guys; here’s my own version of “Unsent,” not quite the same types of men that Alanis sings of, but ones that I consider to be as equally universal.

Dear James,

You were my first of many firsts. The first person to let me know what it feels like to fall in love, how gratifying it could be to have a constant companion, and what a disastrous breakdown of a relationship looks like. I lied to myself to not see the truth of you, but in the end, you taught me how to raise my standards and how valuable honesty is.

Dear Marco,

Meeting you in another country was our greatest allurement and our greatest downfall. I was never able to revert back to the person I was on vacation when you visited me in New York and I’m sorry that I couldn’t be that girl again for you. Italy brought out the unconstraint in me. I’ll never forget how it felt to be drunk off both wine and life, far away from home, feeling satiated from Europe’s seduction.

Dear John,

You came just when I needed you most; a perpetual distraction from my life at the time. Our conversations till three in the morning were my favorite things about you. Unraveling the intricacy of ourselves, considering buried dreams, and unmasking adolescent-old secrets. If only it were easier to remain friends after such attachments; friendship from the beginning would have suited us better.

Dear Ben,

Our time together was short lived, as I believe it was meant to be. I felt both adored and used after leaving your apartment; the right amount of infatuation to keep me coming back and just enough detachment to send me looking elsewhere. For that moment, we both suited each other, and there were a few occasions where I saw the genuine person in you, but it wasn’t enough to keep me around to see more of him.

Dear Sam,

I first remember being intrigued by your face. You liked my voice and how I asked if I could kiss you. Physical attraction was the base of our connection; I could never fully relate or touch through to you. I was trying to find myself back then and you were trying too hard to be something you didn’t fully understand. I take only good memories from you and hope you still think of me the same way too.

Writing a letter, with the intention to send it or not, is like a sense of catharsis. Even though the recipient may never set eyes on your thoughts, you’re confronting a part of yourself that may still be holding on to an outdated chapter of your life, and by addressing those people, you can set them free.


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