To all the boys I thought were the one…

Chloe Holdredge
4 min readMar 9, 2022

The first one: The boy with the white collared shirt.

Like all origins and beginnings of any story, this particular one begins with my first crush. It was only ever a crush, a thought, and an imaginative experience that purely played out in my mind, but never in real life. I had just moved to a completely new state, in a new town, in my 4th-grade year at a new school. I knew nobody and I was scared shitless. Before this year, I had never thought about boys in any sort of way other than what I had seen in movies and TV. A romance, a prince, or someone to eventually sweep me off my feet and save me from whatever treachery I may be in, was my idea of love. My best friend was a boy at my old school, and I never thought anything of it. Growing up with a brother and a boy best friend, kept me a rough and rugged tomgirl. Almost every day, I wore my hair slicked back in a tight high pony with a t-shirt on and black athletic pants. My mother tried to get me to wear anything else, but I simply refused. Comfort and mobility were my main goals. The only day I let my mother dress me was picture day. She had chosen a nice blouse for me and a nice pair of jeans. Picture day was the day I first spotted him. It was only a few weeks into the school year, but I thought I had already seen all the other fourth-graders at lunch or recess. I had never seen him before. He was wearing a white button-up with the sleeves rolled up to the elbows, a nice pair of jeans, cowboy boots, and his hair slicked cleanly. He was the most handsome boy I had ever seen in real life, with strong bone structure, tanned skin, and big brown eyes. He was talking to a bunch of other boys but seemed to be the one at the center of the group. His smile was so big that I could see all of his bright teeth from the other end of the hall. Before I knew it, he was gone down the long hallway. My heart fluttered in my chest, my cheeks blushed, and for the first time, I felt excited about a boy. I thought to myself, “this is it, love at first sight, just like the movies”.

I waited until lunch recess to spot him again. I hoped that he was indeed in the same grade as me so I would see him again. I had made a few girlfriends at recess and we would only hang out by the gymnast bars or play foursquare. Our school had a huge field that I had yet to go on. I scanned the entire playground for the crisp white shirt and there, darting across the field, was a flash of white. It was a sunny day, so I convinced my friends to go out on the field with me and play. He and his friends were playing some sort of duck duck goose game that involved a lot more chasing and running around than usual. He was ridiculously athletic and lightning-fast. I didn't play with them or go say hi but instead stood nearby and occasionally watched him when he wasn't looking. This became an act that I would repeat for the rest of the school year. In my mind, being mysterious and acting uninterested would draw him to me. It never did. It did give me something to look forward to every day. Every pass in the hallway or watching from afar at recess kept the excitement alive. I remember pointing him out to my mom at one point in the school year and she supported my taste. He never knew I liked him then, and I don't believe he ever found out. I created scenarios in my head about us talking, falling in love, and getting married. I never actually spoke to him until high school and my first ever “boyfriend” in the fifth grade was one of his friends. Growing up, I always kept tabs on him and what he was doing. He was a football and track star, always kind, very popular, and always had a steady girlfriend. As a freshman in high school, I remember leaning over to my friend at an assembly, pointing at him, and saying, “One day he’s gonna be my boyfriend”. She laughed knowing it would never happen, and it never did.

Today: The boy with the white collared shirt married his high school sweetheart. He broke records in track at high school. He is now a firefighter and still lives in our same small town. As far as I know, he is still a kind soul.

In some ways, I am glad I never tried to speak to him or play out my fantasies. I feel that at the time I would have only been disappointed because they wouldn’t have met the expectations I held on to in my head. I didn’t realize how much of a hopeless romantic I was, till I finally had my first crush. The constant thinking about him seemed to bring him into my existence more and more in that 4th-grade year, and even years after. Although he didn't date and marry me as I had fantasized about, he did in fact live out that reality with someone else and became exactly who I thought he was, a good man, a good husband, and a townie.

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Chloe Holdredge
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I write true stories about all my ex boyfriends….follow along for all of the juicy tea.