it's complicated

Going Out With My High-School Crush Reignited All My Teenage Insecurities

Photo: J.V. Aranda

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It seemed almost too good to be true. Here I was, sitting in a bougie Greenpoint pizza place across from — finally, after all these years — my high-school crush. Inside an adult woman’s body, my 16-year-old self was freaking out.

Ten years earlier, my adolescent brain was consumed with scenarios like this one. Each moment not spent agonizing over AP Biology was spent agonizing over the argyle sweaters he wore, the Radiohead remixes he listened to, the string quartet his parents forced him to rehearse for until his fingers bled. Everything about him was so awkwardly romantic; so unlike his snot- and pot-covered peers.

While my feelings for him were perhaps painfully obvious — I once showed up to his birthday party and gave him an original pressing of the Beatles’ Abbey Road — I never vocalized them. My sweat-stained cardigans, cyst-speckled face, and lack of a fake ID existed as constant reminders that I was romantically useless to anyone, especially him.

Of course, as is usually the case with these stories, the years passed, the Accutane worked its magic, and I learned that only the worst kind of people truly enjoyed high school. Confidence-wise, I learned to adopt a “fake it till you make it” approach, a strategy that came to serve me well in my dating life.

So imagine my sheer delight when said high-school crush — let’s call him Ryan — relocated to New York City and asked me, after months of liking my selfies, if I wanted to “hang out.” I’d come so far, emotionally and dermatologically, and now I could finally show him. As we made plans, I felt my heart flutter just as it had when I noticed him at the other end of the orchestra classroom. The only difference was that, now, I was a powerful, sexy writer on the brink of success — and, as I soon learned, he was now bald, and nothing like the fantasy I’d built up in my mind.

It didn’t matter.

* * *

Psychologists believe that “emotional regression,” a term coined by Sigmund Freud, is either a conscious or subconscious defense mechanism against any one of life’s many stressors — work, school, fraught encounters with former cello prodigies. In order to cope with this stress, an individual reverts to (typically negative) patterns of behavior from an earlier period in their lives, when the stressor didn’t exist or was easily assuaged by an authority figure, like a parent or teacher. When a student storms out of class after receiving negative feedback on a project, for example, perhaps they are regressing to a time when they were young and more constantly praised for their intelligence. When an adult woman chooses to date someone with whom she truly had nothing in common, solely to prove to herself that she really is lovable — well, you can probably guess.

Maybe I should have seen it as a sign of things to come when, after our first kiss, all I could sputter was, “Oh, wow. You know I had such a crush on you in high school, right?” He laughed nervously and looked around, as though to make sure no one else had overheard. A decade ago, that would have meant social suicide.

A month or so into our new affair, I headed out of town for a three-week trip to Japan. When I returned, ready to launch myself back into this new relationship, I instead ended up launching myself straight into the past. I became, I’m sorry to say, a reincarnation of my high-school self.

Ordinarily, I’m not one to tolerate bullshit from the people I’m dating. I don’t have a “three strikes” policy, I don’t worry about staying friends with my exes — I cut things off and I move on, walking lighter and drama-free across my burned bridge.

This is all to say that when Ryan’s behavior became increasingly flaky upon my return, my typical response would have been to simply end things. Instead, I felt something rising from the depths of my person, something that encouraged me to throw emotional intelligence to the wind. I couldn’t help but feel entitled to a romance for which I had literally waited years, and I wasn’t ready to give up on my teenage fantasies of having Thom Yorke officiate my wedding to this man — which meant that I’d pile on the drama if it kept the weak flame between us flickering. I was going to be loved, even if it meant I had to throw the world’s most passive-aggressive tantrum.

* * *

As so many good tantrums do, it began with a selfie. I posted sexy pictures on Instagram with captions asking about the whereabouts of a single decent man in this cold world, then followed them up with cryptic tweets and meandering blog posts about my loneliness. Anyone watching from afar must have seriously questioned my stability.

It was dangerous how effective these techniques were at conjuring a fresh text from Ryan.

Still, in the weeks that followed, he was always busy when I asked to see him, always neglecting to text back. Instead of letting it go, I breathed in this excess of humiliation until I was choking. I didn’t want to take the hint. Being with him made me feel like a teen again, but not in some joyful, exuberant way — no, it made me feel like I was that gawky kid utterly convinced of her own unlovability, I was in a full-on self-esteem backslide, and keeping his affection felt like the only way to stop it.

Needless to say, it didn’t work. Even as I sit here remembering the whole thing, I’m overcome with an urge to reach for my cell phone, search for Ryan’s name (now a ways down in my message history), and text something nasty. But each time I start typing, I force myself to remember that my problem isn’t really with him — it’s with the insecurities I thought I outgrew like a bad case of cystic acne. Some scars just stay with you.

Dating My High-School Crush Reignited My Old Insecurities