I Finally Hooked Up With My High School Crush A Decade Later — And It Was Not What I Expected

Most people can think of at least one person that they consider “the one that got away.” Maybe the timing just wasn’t right for whatever reason, but you can’t help but wonder what it would be like if you took a swing at it now.

Before you do, be aware of my advice, because I did finally hook up with a high school crush, about a decade too late. I wish I could tell you that it blew my mind and exceeded my expectations. Unfortunately, this is a cautionary tale about how sometimes that long-time fantasy you’ve had should just stay a fantasy.

The First Time We Met I Was In Grade 9

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Photo Credit: James Leynse/Corbis / Getty Images
Photo Credit: James Leynse/Corbis / Getty Images

I spent four long awkward years in high school side-glancing at the handsome older blonde boy every time he went past. Pretending I wasn’t watching only him when I went to the boys’ hockey games, coincidentally parking my car close to his in the school parking lot.

He was dating a cute little blonde girl from my grade — but it was high school, people broke up all the time and I was waiting for my time to shine.

A Few Short Interactions With Him And I Was Hooked

Two teens sit on cement wall, both wear converse with their feet dangling.
Photo Credit: Dương Nhân / Pexels
Photo Credit: Dương Nhân / Pexels

We ran into each other a few times at arenas and parties, only ever saying a few words to each other here and there.

But those encounters were long enough for me to cling to even as I started dating my first serious boyfriend.

He Finally Asked Me Out But I Was Dating Someone Else

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Photo Credit: Cody Black / Unsplash
Photo Credit: Cody Black / Unsplash

It finally happened in a weird Facebook interaction when I was 18 — he asked me to go for a drink sometime. Who was going to break it to him that I wasn’t even legal drinking age?

Instead of acting on my burning desire to say yes, I did the responsible thing and turned him down out of respect for my then-boyfriend. Maybe things would have been different if I said yes that first time.

When I Was Finally Single, He Was Not

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Photo Credit: Niki Sanders / Unsplash
Photo Credit: Niki Sanders / Unsplash

Fast forward about four years. I was finally single and knew exactly who I wanted to go after next. After all, he’d always been there in the back of my mind. Of course, the universe had other plans.

When I was single, he was dating a super cool chick that was basically half my height and had long blonde hair. She was the exact opposite of what I look like and I was well aware.

I Played The Long Game For Years (I Had A Life Too Don’t Worry)

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Photo Credit: Kindel Media / Pexels
Photo Credit: Kindel Media / Pexels

Undeterred, I played the long game, and I don’t mean long like six months. I mean long like another 5 years. For an entire decade, I was a secret architect keeping dusty plans for this dude in my back pocket, tweaking them here and there as both of our lives changed.

Small towns make it easy to manipulate where and when you’ll run into people. Especially if you know the bars they hang out at and the beaches they frequent (there’s only two, and they’re small). Basically what I’m saying is that when the stars aligned and we were both finally single, I knew where to make my first attack.

I Had Unintentionally Built Up My Expectations Way Too High

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Photo Credit: Dario Fernandez Ruz / Pexels

It worked, for the most part. We started a light flirty text relationship which revealed to me that he was a bad texter and I cared way too much about talking with him. That should have been my first red flag — it’s always dangerous to be over-invested.

Looking back, when we made plans to hang out I already had a whole freaking decade of expectations built up in my head, so much so that there’s no way the actual moment ever could have lived up.

Don’t Nervous Drink On A First Hang Out

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Photo Credit: Mathilde Langevin / Unsplash
Photo Credit: Mathilde Langevin / Unsplash

I fully take credit for how fast things went downhill the night we eventually met up. The interaction seemed a little forced and chaotic instead of chill and laid back.

I was so nervous to finally spend time with him that I drank my weight in wine and turned into a hot mess express. I somehow believed that it was now or never. I was too far into the plan and I couldn’t back out now.

The Next Morning I Felt Disappointed Instead Of Satisfied With Myself

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Photo Credit: Maddi Bazzocco / Unsplash
Photo Credit: Maddi Bazzocco / Unsplash

It was one of the weirdest experiences of my life. I remember his bedroom being so dark in the pitch-black night that I actually fell off the bed. Instead of it being funny-cute it was awkward and super weird. It goes to show how easily someone can change a mood by just laughing a situation off.

The next morning came and went, but instead of feeling like I’d finally gotten what I wanted all these years, I just felt disappointed. He wasn’t exactly Prince Charming, just an average dude that I had over-romanticized in my head.

In True Hot Guy Fashion, He Totally Ghosted Me

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Photo Credit: Samantha Gades / Unsplash
Photo Credit: Samantha Gades / Unsplash

To make matters worse, he totally ghosted me after that. I’m talking unanswered messages, muted on Instagram, and possibly even blocked on Snapchat. Nothing bad ever happened between us, we just never hung out again after that night. I’ve always kind of wondered if I said or did something that upset him.

I saw him later that summer at a bar. He was really cold-shouldered which stung a little. Then I saw her, he was with his new girlfriend, a small, blonde girl looking tiny and delicate standing next to him.

Years Later I Still Wonder If I Said Or Did Something Wrong

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Photo Credit: Felipe Cespedes / Pexels
Photo Credit: Felipe Cespedes / Pexels

I was back at the beginning, with nothing to show for it except a fuzzy memory of drunk sex in a room so dark I couldn’t even see myself, let alone him.

It’s been years since that night, and I’m still haunted by those unanswered messages and open-ended questions. I’m not sure why I never heard from him again after quite literally ten years of cat and mouse flirting.

I Would 100% Take That Night Back If I Could

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Photo Credit: Everton Nobrega / Pexels
Photo Credit: Everton Nobrega / Pexels

If I could take one night back in my life it would be the night that I finally hooked up with my high school crush, because it was a huge letdown. I suppose it did teach me that some things are just better left to the imagination.

The strangest part of it all is that some crazy little part of me still wants to run into him again so I can try and redeem myself. Someone save me from me.