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An Open Letter To My High School Ex

An Open Letter To My High School Ex

I’m not sure what sprung on this letter. It’s been months since we’ve talked. I guess I have been wanting to write this for some time really. Writing a letter to your high school ex can be very therapeutic and help you learn a lot about yourself.

Dear Aaron,

It has been over a year since we broke up, yet for some reason I find myself sitting here in my dorm room at 1 AM, staring up at the fluorescent fairy lights above my bed, thinking about you. I’m not sure what sprung on this letter. It’s been months since we’ve talked. I guess I have been wanting to write this for some time really. You see, we went out for what feels like ages ago but also just yesterday. That’s the best way I can explain it. We were so young, so different. Yet, sometimes the heartache of our hasty break up and awkward encounters that ensued still seem to cut deep whenever I think about them.


We went out for almost a year.

I told you I loved you by writing it on a love locket latched to a bridge in Italy. You brought me ice cream and Reese’s when I was sick. We really had a great, supportive relationship. You were so nice… so so nice. I still have yet to meet a guy who’s as genuine and honest as you are. Towards the end of our relationship, I felt like you had began to get annoyed by me because I couldn’t spend as much time with you or because I wasn’t as smart as you. I had all of these thoughts rushing through my head that I wasn’t good enough and you were deeply upset with me.


I still remember that night.

We sat in my car in your driveway, your hands enclosed around mine, as I told you that this couldn’t work anymore. All of my carefully planned words escaped me and the only words I kept muttering were “we are just never on the same page.” I felt your hands slowly slip away from mine, a sigh leaving your lips and nothing else. You weren’t in school the next day. I wondered what you thought of me. I wondered if you had any idea that I had to stop at my best friend’s house on the way to yours because I was crying too much to drive. I wondered if you knew how I talked to your best friend  (and mine at the time) John, asking him for advice, telling him that I understood if he couldn’t talk to me for awhile because I knew he needed to be there for you.

The next few months were strange.

We didn’t talk for a month, our lunch table had split into two, John and I barely spoke and people at school would still ask how our relationship was going. We first spoke on New Years Eve and I realized how much I missed talking to you. I think the worst part of heartbreak is that you can be the closest to someone that you’ve ever been and then in a matter of an hour become strangers. It’s a cliche but cliches wouldn’t exist if there wasn’t some truth behind them.

We went out once in awhile for coffee or lunch, trying to sustain a friendship that wasn’t fully ready to begin. Each of these short meetings left me with this deep hollow feeling in my chest that I had made some kind of mistake. I told my friends but they told me to keep it to myself, that I couldn’t possibly throw caution to your emotions after what I had done. I knew they were right. Yet of course, on one drunken night I asked you to pick me up from a party. I was a mess, slurring and asking you to take me to Wawa as an excuse to spend more time with you. I spilled red slurpee all over your mom’s car and soon after you dropped me off, texted you that I still had feelings for you. You said that we should talk about it the next day, so we met up at a diner and then proceeded to completely avoid the topic. I texted you after and told you how I felt, how I wanted to have fun with you over the summer and enjoy our last few months together before college. Of course, you maturely told me how you may have wanted that in the past but you were over me and it was a bad idea.


I knew that answer was coming and I deserved the complete awkwardness that ensued.

I erased all of the progress we had made after the breakup. Only a few weeks later, we went to the beach with our senior class and I wondered if you knew how I spent a solid hour crying to my best friends after you hooked up with a beautiful, intelligent, popular girl I was friendly with. I had some flings of my own and I wasn’t mad at you or at her, just upset with myself for letting it cut into me as deep as it did. I was, for the most part, content with being single and having fun, but there was always a piece of me that longed for the days of facetiming while you were in Norway or cuddling on my basement couch.

We made plans to meet up for coffee one day before we both left for college, but you were an hour late and I eventually left.

I felt so dumb for thinking you cared, for thinking that it might still matter to you to see me before we parted ways. We did get lunch a few days later and it was nice; we promised to stay in touch while I was at Wisconsin and you were at Penn State. I texted you after your first week and you told me how everything was. That was the last time we spoke. I never received a text asking how the football game was or how my new friends were. Nothing. I’ve got to say that it really hurt. I know that our relationship was weird and we were kind of friends and kind of not. Still, I really thought that I might cross your mind sometime and you would text me out of the blue just to see how I was. I wondered if you knew how hard those first few months were for me. I never realized how hard it would be to completely start over and make new friends. I wasn’t myself at all.

Now that I am nearing the end of my freshman year, I am extremely happy with the way things are going.

I love my friends, my sorority, and everything else about my school. I have learned more about myself in these few months away than I have ever learned at home. I have always wanted to send you a text, or send you a letter, that explained everything. I wish I could explain that all of those times I accused you of not being comfortable around me, I was really just projecting my own insecurities on you. I didn’t have the perspective to realize this at the time, but I know now that I was extremely self conscious. I would cancel on you last minute because my skin was acting up or I didn’t feel like putting on a full face of makeup to sit in my basement. I couldn’t bare the thought of you seeing me without makeup or without perfectly shaved legs. I had no idea that all of these crazy insecurities were giving me anxiety, all of which I pushed onto you and pretended that I was doing nothing wrong.

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I have always wanted to apologize for that. I really had no clue just how focused I was on my appearance, and that was a problem I needed time and distance to work out on my own. I don’t want you to think that this is a cry out for attention or a plea to get back together, but I want you to know how much I appreciate what an amazing boyfriend you were. I still compare all of the guys I meet in college to you, all the while knowing that there is no way they can be as friendly, considerate, and caring as you are.

I hope that Penn State is treating you well and there is no doubt in my mind that some day I’ll see you on some Forbes 100 Greatest Minds list or on the presidential ballot.


I wish you all the best,


Have you ever a written a letter to an ex? Let us know in the comments below!
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