I Classically Nabbed my High School Crush Who Was “Way Out of My League”

Gillian Sisley

This love story is straight out of a blockbuster rom-com.


Photo by moren hsu on Unsplash

Let me set the scene for you — picture your every day, North American high school.

The new school year has begun, and students flood back in. A young, somewhat chunky brunette with a bob and glasses walks into the school in skinny jeans, a graphic T and a pair of high-top Converse. This is her unofficial school uniform — she’s certainly not popular by any means, and really only keeps to herself and a few close friends. Actually, she’s still in classes with a lot of the people who bullied her in junior high. She can’t wait to get out of this place and never have to see any of their b*itchy faces ever again!


Photo by Camila Damásio on Unsplash

No matter how hard she tried in junior high, she simply could never be anything other than herself — so she never fit in. Because she was intrinsically quirky and creative, and those generally weren’t traits to have to be popular.

And just to clarify, we’re not talking “cute quirky” either, like “Zooey Deschanel” quirky. We’re talking weird, outcast, a little out-there quirky — she spent most of her time in school animatedly painting in art class or scribbling short stories in her notebooks while not paying attention to lectures.

The “moment” the crush appears.

I remember that it was pretty early into the school year when I saw him — I was in the 11th grade, and I was walking down the halls to class. He was walking with a group of friends, and I had to do a double-take because I couldn’t believe this was the same guy I had seen in the halls before.

And trust me, I wasn’t the only one looking.

You know those scenes in movies when a kind of plain-joe comes back from summer vacation and just has this totally different “quality” to him? Suddenly, all the girls who were looking past this guy are turning heads to see him walk by? This was him, the male main lead in our story,

He’d always had a sweet face with a cute quality — I remember thinking this about him when I saw him around in general the previous year. But during the summer, he must have dropped something like 50+ pounds (he was a pretty big guy)— and suddenly that “cute” face was replaced with a chiselled jawline and an undeniably handsome disposition.

He looked less like a boy, and more like a man.

Damn, he was stunning. I, on the other hand, was not. So while other girls chatted him up, with his newly developed manliness and his new wardrobe which was seemingly now free of over-sized t-shirts and baggy jeans — I admired from afar. I would never get a guy like that.

Not a girl like me.

He was that stereotypically “nice guy” with painfully dashing looks. And it wasn’t fair.

Think back on your time in school — there are a very few, select people who you can remember who were just incredibly nice people. Even though they hung out with the popular crew, they were still just kind and humble.

He was a floater — could seamlessly fit into any group at any time and was welcomed with open arms. He was an easy character to be around, with a gentle disposition and a warm smile. He never had one bad thing to say about anyone. He was a quintessentially nice guy.

He was also a senior, so after a year of watching from afar and glancing at him sheepishly in the halls as I passed his locker, he graduated from our school.

Another summer came and went, and I would return to school in a few new sets of skinny jeans, graphic Ts and Converse for the new school year.

I was going to miss seeing his face in the halls.

Enter the “damn, that sucks” moment for our heroine (aka. me).

I returned to school to animated chatter in our classrooms. A few girls in our classes had started dating new guys, but I honestly didn’t pay much attention to any of it.

A few gaggles of girls, who I had traumatic memories of being bullied by, were all up in sorts, looking at pictures of the senior prom that took place right before the summer.

One of the girls, in particular, was showing off pictures of her dress and the date she’d gone with — he was a year older, and they had begun dating a few weeks before school ended…

Yup. You guessed it.

There he was, in a picture with her, with his blown-back hair and his hipster Ray-Ban glasses and a stunningly handsome black tux.

Man, that stung. Stung so f*cking much. More than I ever thought it could.

Because this girl he was dating — she tormented me in junior high. I borderline loathed her and she just wasn’t a good person. And he was so damn sweet… how could he choose her, of all people!?

I hated it… and I specifically remember thinking, “Damn… if that b*tch can get a guy like that, what the hell is wrong with me?”

I looked over at her, in her jubilant happiness because she’d nabbed the most incredible guy in the world, and thought to myself,

“You just wait and see… all of you. I’ll get a good one, and I’ll shock you all with how amazing he is! You’ll be jealous!”

Fast forward to the “meet-cute” years later.

Four years pass.

I no longer care whether the girls who bullied me in school will be jealous of the person whom I date — I deleted every single one of them off of all my social media accounts literally the day after graduation and it was amazing.

I went on to study at university for a bachelor’s degree. I studied abroad in China and South Korea for a few months, travelled to Japan, and made a real adventure of my post-secondary years.

By this point, I had updated my fashion sense somewhat. I swapped my little brown bob for long blond hair, my graphic Ts for cardigans and my Converse for leather ankle boots — you know, classic university-style from stores like H&M.


Photo by Caleb George on Unsplash

Until recently, I’d been working at a hardware store part-time. The store closed down, and most of the employees left, while others transferred to different stores. It was the summer after graduating from university, and just before starting my Advanced Diploma program in Public Relations.

I was hanging out with one of my girl-friends who I’d worked with at the hardware store, and was lamenting about how so many of my school friends had moved back home or away (my best friend moved to Montreal to study her Masters in Opera), and so essentially I was feeling like going into this new school year was going to be extremely lonely.

“Well hey, how about this”, she begins, driving us to our favourite Chinese restaurant in her Volkswagen GTI. “Some friends of mine live in this house together outside of town — they’re friends from work, at the new hardware store I transferred to when ours closed down. They’re having a party this weekend at their place — we call it the Frat House — you should come.”

I wasn’t really in the mood to make new friends, but hey, why not? I certainly wasn’t the “party-type”, but this sounded like it would be an interesting time.

She said she would pick me up and drive me there.

Fast-forward to the day of the party. My friend texts me saying she has two of the guys in tow, and will arrive shortly. I’m wearing my bikini (the Frat House had a pool) under a white sleeveless button-up and a pair of turquoise lacy shorts. I don’t know if I was dressed to impress, but I was dressed for something.

She pulls up to my parent’s driveway, and I slip into the backseat behind the front passenger. I introduce myself to the guy on my left, and as we’re pulling out of the driveway, my friend says as she indicates to the guy in the passenger seat, “You guys might already know each other — he went to school with us, and his ex was one of your classmates.”

It felt like time literally slowed to a halt as I watched him slowly turn his head to look back at me and introduce himself.

I honestly almost shit myself right then and there.

Not only had he become far more incomprehensibly handsome than in high school, but DAMN you could grate cheese on that jawline it was so sharp! And is that a half-sleeve of tattoos on his left arm? Lord have mercy.

I couldn’t believe that, of all people to be sitting in that front seat, it was him — my high school crush.

And he was even further out of my league than ever before.

Cut to the scene where the heroine makes an utter fool of herself (obviously).

So I’m at this party and I’m definitely not cool enough to be there, but I’m thinking I’ll make the most of it. More than anything… I want to talk to my past crush, even if it’s only some small talk.

Hell, who am I kidding? He’s 100% my current crush and utter heartthrob who I’ll be daydreaming about for the rest of my life. DAMMIT.

I was kind of sticking out like a sore thumb. All I could do to calm my nerves was drink, so I did… I drank a lot. I drank until I had the courage to walk right up to my crush, trying to act super chill and laid back to start a low-key conversation.

Only, I wasn’t any of those things, because for some horribly awful reason I thought being “chill” meant screaming in his literal face, “I WANT TO GO IN THE POOL!”

He stared at me, a little taken aback, and said, completely deadpan, “Then go in the pool.”

Cue scurrying off, hiding behind a corner, and legitimately putting my face in my hands out of embarrassment and saying out loud to myself, “Oh my God, what the f*ck was that? What is wrong with me?”

You could say I won him over with my charm and adorable quirkiness.

Despite the fact that I verbally assaulted one of the main members of the friend group, they kept me around (even adding me to their infamous group chat).

I figured out really quick that this group of friends were seriously just incredibly down-to-Earth, good-hearted people. Most of them worked as truckers or laborers, and there were a few drinking problems here and there, but honestly, everyone had a heart of gold, and they didn’t put up with any dramatics or unnecessary bullshit.

These were my kind of people.

I remember being at a bonfire, (I think it was my 3rd time hanging out with everyone?), and the guy who had been sitting in the back seat with me in my friend’s car (also known as the best friend of my crush), turned to my girl-friend and said about me, “I like her — she’s really funny”.

My girl-friend nodded, replying, “Yup — she’s one of us now.”


Photo by Tegan Mierle on Unsplash

I pretended not to overhear the conversation from across the fire, but the smile of pure delight that must have been on my face was undeniable.

Throughout the next several months, I came to every hangout and became a regular member of the crew. I would make an effort to look extra good because I knew my crush would be there.

We chatted from time to time about school (we were the only two in the group who had gone to university), and actually had a lot in common as far as values, goal-oriented drive and a passion for learning. We also found out that not only were we attending schools that were just a few blocks away from each other, but we had been riding the exact same bus route for 4 years, and never noticed.

A little voice in my head told me it was fate.

After enough hangouts, we had the one that locked us in for good.

We got snowed in at a friend’s apartment, and I don’t know how else to tell you this, but something invisible and powerful changed in the atmosphere between us, and in the blink of an eye, this impossibly strong bond was formed that weekend.

Neither of us knows what really happened that night at the apartment — but we’ll both be saying for the rest of our lives that in a literal split second we somehow went from being acquaintances to feeling like we’d been seriously dating for years.

The connection that formed was instant, powerful, and completely indescribable.

Only, wait, that’s not true. It’s not indescribable.

It was the exact moment, at the exact same time, that we both realized we were truly meant to be together — that we were in fact soulmates. And there was literally no other way to explain it.

For every moment I sheepishly glanced him at his locker in high school, and watched as other girls chatted him up, and smiled to myself when I would see him beaming and laughing with his friends… little did I know then, but every single moment I was staring at him, I was looking at my soulmate.

It just wasn’t the right time for us to be together yet, not back then. We still had a few more things to learn and mistakes to make before we were ready to be enlightened about our role in one another’s lives.

And now, 3 years later, we own a house together, we recused a high-maintenance Shih-Tzu, I’m wearing a big ol’ diamond ring on my left hand, and our wedding day is in 5 months.

If this isn’t a cheesy, yet heart-warming, real-life rom-com, then I don’t know what is.

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