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The Unsent Letters To Your Exes: How Addressing Your Past Will Set You Free

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Have you ever written a letter to an ex-boyfriend to articulate the things you left unsaid, only for a sense of closure, but not send it? I’ve done it 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, leading my heart to drop into my stomach and knots to fill the void.

The lyrics to Alanis Morissette’s song, “Unsent,” are comprised of letters to her former boyfriends. Although the song contains personal accounts of Morissette’s relationships, the types of men she depicts in the lyrics make it relatable for most women.

There is the guy she likes, who is unavailable; the bad-boy heartbreaker; the “too nice” guy with whom she plays games; the adventurous, yet also dangerous guy; the one with whom she learns the most about herself.

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recipient may never set eyes on your thoughts, it forces you to confront a part of yourself that may be clinging to an outdated chapter of your life. By addressing those people, you can set them free.

Below is my own version of “Unsent”:

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 in you, but in the end, you taught me how to raise my standards and the value of honesty with oneself.

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.

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 and your company.

Dear John,

You came when I needed you most. You were a perpetual distraction from my life at the time. Our conversations until 3 am were one of my favorite things about you, along with unraveling our intricacies, considering buried dreams and unmasking adolescent 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; I felt 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 when I saw the genuine person in you, but it wasn’t enough to keep me around to see more.

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 your soul.

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.

Photo Courtesy: We Heart it