There's a moment in every young boy's life when a wave of bravery washes over him, and he proceeds to do something so extremely bold, so intensely daring, and, of course, so mind-numbingly stupid. For me, that idiotic moment came on Valentine's Day in the seventh grade. 

Her name was Chloe. She was a new student that year, changing school districts as a result of a tough divorce. From the moment I first laid eyes on her, I was infatuated. Her wavy brown hair that she would play with constantly. Her deep blue eyes that gave off the slightest essence of sadness, and in which you would get lost and be overcome by a feeling of calm. The small smile and laugh she would give every time someone would start a conversation with her. Taking all of that and mixing it with the weird thoughts and feelings going through my teenage mind and pubescent body, I became the epitome of hopelessly in love. 

I spent a good amount of the school year admiring her from a distance, for I knew I didn't have a chance with her. Childhood hadn't necessarily been kind to me, giving me an overweight body with no athletic ability or coordination, giant braces trying to tame my gangly teeth, and a face only a mother could love. It's safe to say that I was never invited to any boy-girl parties.

Like all guys who have no luck with the ladies, I adopted the mindset that I was a "nice guy" who would "treat a girl the proper way." That, coupled with growing up watching romantic comedies and other chick flicks with my mother and two older sisters, made me certain that I was a hopeless romantic who just needed one opportunity to show my true colors. After all, it's what's on the inside that matters, right? 

It was the week before Valentine's Day, and I sat in history class staring at the love of my life. Next to me was my best friend Danny, or ‘D Dawg' as he was known by in the streets (those streets being of course just his neighborhood, and the only people calling him that were the third graders who admired him). It was that fateful day that Mr. Holm, a bald man with a sharp disdain for all joy and happiness, sparked creativity in my mind. He was going on about boring things, such as far-away countries and their capitals, when suddenly he decided to tell us about the St. Valentine's Day Massacre (I'm sure there was a much better segue into the topic, but I wasn't really paying any attention). 

For those who are uninformed on the topic, the St. Valentine's Day Massacre is the name given to the brutal murder of seven gang members in the beautiful oasis that was 1920s Chicago. The gang members worked for an Irishman by the name of George Moran, or ‘Bugs' as he was known by in the streets (please note that Danny laughed at that later and talked about how much cooler the name D Dawg was than Bugs). Bugs was a longtime rival of the notorious Al Capone, who despised Bugs more than anything. Now, at the time, the two were in a tight competition to earn the title of baddest dude on the block, trying to grab a majority hold of the bootlegging and gambling scene. Capone wanted to make a statement, a grand gesture that would show Bugs who was the man. So in what could be described as a crime of passion, on Valentine's Day he had seven of Bugs' best men killed. 

You may be wondering where this is leading. As I said before, I wasn't really paying attention. So what I heard from Mr. Bald-meanie-head was "grand gesture," "passion," and "Valentine's Day." As I sat in class and watched my goddess chew her bubblegum, an idea was born. I would do something so cute, so clever, so totally-freaking-adorable, that Chloe could never deny me.

***

Fast forward to Valentine's Day the next week. I woke up an hour early. I combed my hair for the first time probably ever since my mom stopped doing it. I took stock of all my belongings. Heart-shaped box of chocolates? Check. King-sized bag of skittles (Chloe's favorite candy, which I learned by stalking her Facebook page)? Check. A toy microphone from a Rock Band video game? Check. I shoved everything in my backpack and waited for the bus. 

I don't know if this is a universal thing, but at my middle school, the busses would drop us off at school, or as it's known by in the streets, ‘Prison,' up to forty-five minutes before school even started, depending on your bus-route. The students would congregate in the gymnasium, sitting in cliques on the bleachers or on the hardwood floor. I happened to be one of the first group of kids to arrive, and I was aware through careful observation that Chloe was one of the last. I got off the bus at school and ran to the auditorium. I sprinted up the bleachers and hid in the corner. Now all I could do was wait for the right moment. 

***

Ten Things I Hate About You capped off a wonderful decade of movies in the 1990s. For those who are uninformed on the film, it's a cheesy 90s chick-flick centered around teens, passion, and romance. There's a very famous scene in which Heath Ledger's character dances throughout the bleachers and serenades Julia Stiles' character with a fun rendition of "Can't Take My Eyes Off You." It's a serious shame that my mother had just shown me that very film a few weeks before. It's even more of a shame that I believed I could successfully replicate anything that Heath Ledger could do. 

It happened so fast. Chloe entered the gym with a group of friends. D Dawg made a weird bird signal sound and then yelled, "Chloe look over there!" Suddenly, I was walking down the bleachers trying to scream/sing "Nothin' On You," a popular song at the time by B.o.B and featuring the then rising star Bruno Mars. The song is beautiful, the perfect pop-hit that's like opiates to a middle-schooler's ears. I still can't hear it without cringing. 

It took me about four words and two steps before I tripped down the stairs. By the time I stumbled my way to the bottom, with a microphone cord wrapped around my legs and a dented heart-shaped box of chocolates in my hand, the laughter in the room was loud enough to deafen me. However I could hear none of it, as I was entranced by Chloe's beautiful face. At that moment, she looked absolutely horrified. I walked toward her and handed her the flowers. I took off my backpack and retrieved the chocolates and skittles for her. I held them out, and she looked at them. Then she looked at me. Then she looked at them. Then she looked at her friends. Then she looked disgusted. 

She began to laugh so hard that the room began to shake (for me at least). She dropped the flowers and turned her back to me, and laughed some more. The bell rang and she swiftly left with her clique, leaving me a red-faced spectacle for the entire student-body to laugh at. You might think it couldn't get any worse. That's where you would be wrong. That's when the puke came. I vomited my breakfast everywhere. What a waste of three delicious Eggo waffles. The laughter intensified. Then came the crying. That's when I decided to run down to the office and beg the secretary to call my dad to pick me up from school. 

***

In that moment, I realized I was not Heath Ledger. I was not Al Capone. Hell, I wasn't even Bugs. I was just one of the seven gangsters killed in that Valentine's Day Massacre. At least it felt that way to me.

It would have been easy to give up after that. Cry to my parents, force them to move me to a different school, or even better, an entirely different state. However, the hopeless romantic in me was still alive and strong. It may be tough sometimes, but the pursuit of love is a journey, and I was prepared to fight on, even stronger than before.

But, the catastrophic events of that day, everyone, is why I hate those stupid 1990s teen love movies.