I Went Out With My High School Crush As An Adult — And It Was A Disaster

I was nervously pulling at the edge of my t-shirt while waiting on my front steps, wondering if I should've worn a dress despite the chilly November evening.

My date—let's call him Tyler—was on time. He greeted me with a hug on the sidewalk. He was so tall; to put my arms around his neck, I had to stand on tiptoes. I was relieved to see he was also wearing a t-shirt.

He looked much the same as he had in high school, when I had had a wild crush on him and he didn't bother noticing me. The only exception was a military buzzcut leftover from his time in the army, which meant he'd lost his soft, silky smooth hair that used to glistened as if it were wet. One afternoon during tech crew, sawdust fell in his hair and he asked me to brush it off because his hands were full holding a piece of plywood. My hands were shaking so badly that I almost couldn't do it.

He still looked good as-is.

"Where are we going?" he said now, on our date almost ten years overdue, his hands in his pockets, walking two steps ahead of me on the sidewalk.

I smiled. The date was going to be at my favorite Indian restaurant. "You'll love it."

In high school, Tyler was 18 to my 16—a cool, grinning senior to my shy, awkward-around-boys sophomore. We met one August afternoon in the after-school drama club, where we were both on the tech crew, building sets. (He liked working with his hands and I was too nervous to be on the stage.)

He was the first boy to ever flirt with me and I was dizzy with the attention. I had never even kissed anyone before, but there he was, pulling out his wallet to show me the condom he always kept there. I was shocked and a little nervous to see it, but tried to play it cool, hoping to seem grown up. The memory of a man showing me a condom for the first time in my life remains in my head to this day.

Much to my despair, and despite the flirting, we never dated in high school. In fact, I never dated anyone in high school. Not because I didn't want to (I did), or because I wasn't allowed (I was), but because I was never asked. I never had a date to a single school dance, never went on double dates with my friends.

Since high school, I've always wondered why that was. I wore a purity ring back then, which didn't help my case. More than that, though, I suppose I was too shy, too unwilling to put myself out there if a boy didn't pursue me first. I didn't know how to talk to boys or get them to talk to me. I was a techie through and through, preferring the backstage shadows to the spotlight.

On the last day of classes, I wrote him a love note, emboldened by the fact that he was graduating and I would never have to see him again if things went poorly. In part, it said: "I guess you probably already could tell because I wasn't exactly subtle about it, but before you graduate, I want to make sure that you know how wild I am about you. I don't expect that to change things, but I just think when someone is liked this much, they should know it." I pressed it into his palm in the hallway before the first bell and ran for my life.

He texted me ten minutes later to say I was very sweet, but he wasn't interested.

That was the first time I began to notice a pattern in my dating life: Men are not interested.

When I was asked out for the first time in college, I was so surprised it was finally happening that I said yes, and would've said yes, regardless of who was asking or what he was like or how I felt about him. I had it in my head that having a guy express interest in me was such a rare opportunity I couldn't pass it up.

That was my motto: Take what you can get from whoever is offering, because they might be the only one to ask.

I'm not saying that feeling started with Tyler, but he was the first boy I'd liked so much that I'd have done anything he'd wanted at 16 if it meant being with him. This meant that every one of his crude condom jokes didn't matter to me, purity ring or not. And despite not enjoying either partying or drinking back then, I'd have gone and done anything if he had only asked. Up to and including taking off my purity ring, I imagine.

But he never did ask.

Fast forward eight years. Tyler and I had stayed in vague Facebook touch—wishing each other happy birthdays, liking each other's statuses, occasionally private messaging to talk about his travels in the military and my academic successes, but never anything too deep or personal. Until suddenly, he was out of the military and living back in our hometown and texting me, asking to take me to dinner.

Maybe I was the only friend Tyler had who still lived in town. Maybe he was hoping for an easy yes, because a yes from the past might carry over to a yes in the present. And I did agree, mostly for the 16-year-old who would've done anything for this chance.

Getting ready, I was a kid acting like I had never been on a date. I changed clothes three times. I put on my favorite red lipstick, then decided it was too bold and took it off. I settled, instead, for a more natural-looking shade of pink, something far less likely to smear. I wondered what we would talk about.

Dinner was excellent. I could hardly believe I was there with him. He was handsome, a little bit of scruff on his chin, and polite. He was funny and kind to the waitress. He was someone my mother would have liked, not the crude teenager cracking condom jokes I remembered.

Which is why I was so surprised when, while waiting for the check, he made a quip about how he should've "faked" PTSD to get money. He was referring to the monthly allowance veterans who had seen active combat receive if they are diagnosed afterward with a mental illness. Tyler told me if he had played his cards right when attending his mandatory therapy session after his tour, he could, he said, be getting paid right now for nothing.

I pushed back on the comment—"You think that's for nothing?"—and we had an engaging conversation on mental health, so I let it go. Even then, I wanted to like this man and for him to like me, I guess because teenage fantasies die hard. This night wasn't for me; this was for my 16-year-old counterpart.

Afterward, I suggested we browse the local bookstore, where I tried to connect with him. The bookstore was one of my favorite places in the city—big wooden doors, cozy like a cabin, brightly lit. All of my most meaningful relationships have come from a shared love of books, so I thought by taking him there I would start to relax. If this was going to go anywhere, the books that mattered to me would have to be part of that foundation.

I took a copy of Star Talk by Neil deGrasse Tyson off the shelf and explained how important his work had been to me in writing the short story collection I'd recently finished.

"Oh yes," said Tyler. "I know him. Black science man."

"Excuse me?" I said, and he showed me a meme on his phone with a quote about the universe, written in a racist use of African-American vernacular, and a picture of Tyson. The quote was attributed to "black science man."

"That's not funny," I said. I looked around, realizing I'd be embarrassed if someone I knew saw us together.

As the night wore on, it didn't get better. In the car, he insulted sexual assault survivors and women seeking abortions—"It makes sense," he said, "that if abortion is legalized only for a woman who has been raped, then the woman should report the rape prior to seeking the abortion"—before I told him to shut up.

There was no one moment in the night where the fantasy shattered. It was more like a Jenga tower—each comment he made was a wooden block pulled from the pedestal I had put him on in high school, until finally the whole thing tumbled down.

Taking me home, he asked if I wanted to get drinks. "We could keep the night going," he said.

"I really don't think so," I replied, and got out without acknowledging his proposal to do this again sometime. Honestly, I don't think he was that into me either—he never called.

I went out with him for the girl at 16 who couldn't get a date, but I walked out for me, because the idea of "taking what you can get" when it comes to men was not the narrative of my life anymore. That night strengthened my resolve to never again say yes to a man just because he asked. I no longer consider being asked out such a high honor that I would be a fool to pass it up.

My 16-year-old self would've laughed at every racist, sexist comment he made, just like she had laughed at every crude joke he made about girls and condoms in high school. She would've been so happy just to be there—with him—that she'd have overlooked anything.

I hope she was watching when I left.