Interviewing My Middle School Crush: A Love Letter to My Former Self

by Emma Herbst

For nearly a decade of my life, I’ve joked, “Once an ugly middle schooler, always an ugly middle schooler” and meant it. People get really offended by the idea that I look back and call my younger self ugly. But, for me, it has always been an objective, empirical fact and one that I’ve always felt very comfortable voicing and writing about. It wasn’t self-egregious or pitying, but, rather, a way in which I could reclaim a time in my life that I don’t look back fondly on. While I can, thankfully, look at myself now and know that I am far beyond whatever limitations my 12-year-old self had, I still very much feel like I will never leave that mentality behind-- that I’ll never be anything more than someone who was made fun of in middle school. 

I grew up in Oxford, Mississippi-- a college town about an hour outside of Memphis-- where everyone knew everyone, where everyone’s parents knew everyone’s parents. Oxford is beautiful and iconoclastic against the backdrop of the Mississippi Delta but I never truly fit. The phrase “not fitting in” is one that I think can easily lose its meaning through overuse. I wish my “not fitting in” was in an idyllic way or in a way that I could laugh at as an adult, but my “not fitting in” was gritty and traumatic and is very much immortalized as an emotional burden I carry every day, nearly ten years later. 

I hit puberty really late which didn’t help the fact that I had already felt emotionally separate from everyone I was at school with. By the time I was twelve, somehow everyone around me looked like women while I was still an ugly middle schooler. I didn’t get cast in musicals because I didn’t “look the part,” I got picked on by the older eighth-graders because of my weight, and, of course, got asked out by boys as a joke. 

About three weeks ago, I jokingly suggested to the staff at The Rival that I should “interview my middle school crush for Sex Week.” At the time, it seemed funny and trivial-- a low-stakes, relatable piece I could put out and forget about by the time my next deadline rolled around. It ended up being something entirely different.

While I certainly won’t speak to the universality of this, I am very much someone who was fundamentally shaped by the boys I liked in middle school. A lot of my core interests are ones that were formed during this era of my life and, tangentially, can be traced back to my desire to share interests with the boys I liked. I was self-aware enough at the time to know that I was definitely no catch. I certainly didn’t feel pretty and I think a part of me knew that I looked different than the statuesque blondes I went to school with. I used my interests in place of that confidence-- I would always have something to talk to someone about. But deep down I knew I wasn’t playing the same game as everyone else and I think it’s that self-awareness that keeps me trapped in this “ugly middle schooler” paradox-- knowing that I no longer look like that, but having it inhibit me all the same. 

Of all the crushes I had in middle school, the one that sticks with me is Andrew Gardner. I was absolutely in love with Andrew Gardner (to the extent that a 12-year-old can feel romantic love). He was smart, he was goofy, he was cute, he was talented. There were things that we enjoyed and talked about that made me feel like we were the only two people to enjoy and talk about them. I would go to school hoping that I’d get a chance to talk to him or that maybe he would sit next to me at lunch, maybe even share a pair of headphones. It’s almost impossible to verbalize what it feels like to really crush on someone and without the threat of sounding juvenile, it was a really special time for me. Despite knowing that the feelings I had for him were not the feelings he had for me, there was something so painfully blissful about waking up in the morning and thinking, “Today is the day that he starts liking me.” 

After days of avoidance and on a rare whim of confidence, I ended up reaching out to him. Despite the fact that I hadn’t spoken to him in nearly eight years, I couldn’t help but feel deeply anxious at the mere idea of not only reaching out to him but being vulnerable to someone who had played witness to one of the worst times in my life. As the days approached the interview, I was forced to reflect on why I was still so scared of him-- a normal person who I had once been so close to and whose opinion had once held so much value for me. In truth, I was worried about perception. It’s human, yet certainly a little romanticized and idealistic, that I would want those from my past to look at my current self and remark on how different I was or how well I was doing. But it was this exact expectation that left the day of our interview anxiety-ridden. What if I had been nothing but a blip on his memory? What if he hadn’t remembered me at all? I had spent years wondering what it might be like to run into him and be able to rewrite whatever impression I had left him with eight years prior. Now I was finally getting my chance to do that, yet I was dreading it becoming a tangible reality. 

For years I had been able to use this dream scenario as a coping mechanism-- this “what if” had become my only way of acknowledging how far I had come from the “ugly girl” archetype I had allowed my memory to follow. I wasn’t ready to see how the foundation of my self-worth might crumble if I wasn’t able to live up to the expectations I had set for myself. 

I ended up following through with the interview-- I knew if I let my fear push me out of the opportunity that my bravery had set up for me, I would never get any of the closure I felt like I needed. It was that same anxiety, that same fear, that had put me in the place I was trying to get out of. I went into our phone call not knowing what I was going to get, not knowing what I would leave with and while my intentions for the article were originally comical and lighthearted, I wouldn’t be doing my younger self justice if I wrote that piece.

He told me about the years that I had missed, about the people I no longer knew. We joked about the people we had once been nearly ten years ago and talked about the colleges we had almost gone to. He was perfectly normal. My memory had let me remember him, not as how he was but in the way in which it is easiest to remember someone-- as a fraction of who they were. 

I’m not entirely sure why my crush on Andrew Gardner stayed with me. When I think back on that era of my life, it’s impossible for me to remember it without remembering him despite the fact that there were plenty of boys that I liked as an ugly middle-schooler who didn’t like me back. It wasn’t like I was an adult thinking, “Damn, I really wish my middle school crush would have liked me back!” I didn’t want his belated approval and didn’t feel like I needed it. This became even more clear after our phone call-- not because it went poorly, or that he was a huge douchebag, or thought I was super weird for reaching out, but because he had liked me the whole time.  

I find it quite difficult to put into words just how shocking this was to me. Had he just been really good at hiding it? Had I been so wrapped up in liking him that I didn’t notice that he liked me? How could I have missed that especially as an adult, looking back, with experience in committed relationships? I lingered with these thoughts for days -- as I write this, I still find myself thinking about them. 

They say that every time you recollect or retell something, you’re simply just remembering the memory itself. As time goes by, your memory becomes less and less accurate. I had spent so much of my time rewriting my own memory that I had done my former self a complete disservice. I had been so worried about if Andrew had remembered me that I didn’t even bother questioning if I was the one who had misremembered. In being so consumed by the idea of how others had remembered me, I had lost touch with how I was remembering myself and, in doing so, had become cruel and unforgiving to the person who I thought had been most deserving of redemption. 

It would be lying if I said that the interview with Andrew had been unimportant-- it hadn’t been. But it wasn’t important because of anything he told me, it had been important because of what I realized I hadn’t told myself. It forced me to wonder why I had been so reluctant to consider that maybe, just maybe, I had been too hard on that ugly middle schooler. I have no choice but to unlearn my hatred for her and to allow myself to move on. It would be untrue as well if I told you that I had completely resolved my tension with my former self. I’ve got a lot of healing ahead of me and there’s a lot about me that I need to learn. 

I ultimately decided not to include my interview with Andrew-- it didn’t seem to fit into the piece I felt like I needed to write for myself. It ended up serving more of a personal service than a journalistic one. Just as I am forever indebted to the person I once was, I’m indebted to the original article I set out to write-- one that was universal and relatable. But in the spirit of Sex Week, the most vulnerable and authentic piece I could have written was one for myself, one that was a love letter to my former self. I can only hope to learn from this and to, in the future, look back at my current self with more fondness.