To The Stupid Boy from High School, Whose Shirt I Still Sleep In


My closet is a graveyard of shirts that once belonged to men who are no longer worth my time. However, I often find myself reaching for one in particular, when I need something to sleep in at night. I throw my hair in a ponytail and slip the all-too-familiar, obnoxious shade of blue material over my head. I look in the mirror and smile at the evil Teddy bear that I see on my chest, looking back at me. Usually, I head straight for my bed, curl up under the covers, and go to sleep. Tonight, my reflection hit me differently, and the T-shirt serves as a Time Machine. So now, I sit on my bathroom floor and write.

It is September of 2008, Freshman year. I am 14 years old, and it is the first day of high school. My first class of the day is Algebra, where I can be found sitting at my desk. To my right there’s a window. Outside of it, a tree I have conversations with in my head. To my left there’s a Stupid Boy with obnoxiously blue eyes. I swear he’s staring at me. Or maybe I just wish he was. Actually, I wish I was dead, or anywhere but here. I’m left-handed. He’s right-handed, so we are forced to face each other as we scribble down these equations that I pretend make sense to me.

Nothing makes much sense to me. Except for 4th-hour biology, where the Stupid Boy is assigned the seat in front of me. He takes off his hoodie revealing a graphic T-shirt that is an all-too-familiar, obnoxious shade of blue. On it, there’s an evil teddy bear. I instantly fall in love and tell him I like his shirt. He turns, bats his stupid eyelashes and says, “Thanks, it matches my eyes,” as if I hadn’t already noticed.

Our biology teacher asks questions, and nobody raises their hand. I mumble the answers under my breath while playing connect-the-dots with the birthmarks on the back of the Stupid Boy’s neck. He repeats what I say aloud, so the teacher will shut up. He is praised for speaking the correct answers aloud. Stupid Boy turns to me and whispers “Talk louder, Smart Girl.”

On the day that we get our very first biology tests back, I look down and shrug at the A in red ink. Who cares? Stupid Boy turns in his chair, smirks, and hands his test to me with the giant A+ written across the top of the page. He winks, points at the evil teddy bear, and says “It’s the shirt.”

After that, I swear he wears the damn thing once a week. On those days, I spend most of 4th hour staring at the cartoon monsters on his back. I comment on the shirt every time he wears it.

On the day in December when I turn 15, he lets me borrow the evil teddy bear shirt, “For luck.” I change into the shirt during our lunch break and meet him in Biology. At the front of the classroom, our teacher has all of his student’s grades on display. Stupid Boy and I look at each other and smile as we realize we are the only students with A’s.

It is December of 2009, Sophomore year. I am in my Algebra 2 class. Stupid Boy walks in wearing an obnoxious shade of blue. I walk up to him for the hundredth time, open my mouth to speak, but he cuts me off and says, “Yes, Gina. I know. I like my shirt too.”

I laugh. “Yes, but did you know it matches your eyes? Or that my birthday is next Tuesday?”

He pretends not to hear me and takes his seat.

On the Tuesday I turn 16, Stupid Boy reaches into his backpack and throws something at me from across the room. The thing that lands on my desk is an obnoxious shade of blue.

“Happy Birthday,” He says, “Keep it. There’s a bleach stain under the left armpit anyway.” Stupid Boy laughs and walks away.

It is February of 2010, Junior year. I rush into our first-hour health class. I’m late, so I head for the only open desk in the classroom. As I walk past, Stupid Boy holds eye contact like he knows there’s an evil teddy bear under my hoodie. I sit in front of him, unzip my hoodie and put it on my chair. I can feel his obnoxiously blue eyes behind me, staring at the familiar monsters on my back for the rest of the hour. I pretend not to notice or care.

It is August, 2011. Exactly one week before the beginning of Senior year. I am 17 years old, sitting on my bed after reading Markus Zusak’s Book Thief, cover-to-cover for 14 hours straight. With tears streaming down my face, I blindly reach for an obnoxious shade of blue in the pile of dirty laundry that has taken over the floor of my bedroom. I ball up the T-shirt and blow my nose right in the evil teddy bear’s face and wonder if Stupid Boy finished his A.P. summer reading list yet. I wonder if this book affected him in the same way.

It is May 2012, on the night before the very last day of high school. I am 18 years old. I can’t sleep. I need to study for my very last day of finals, but I can’t stop crying because all I can think about is the funeral of a friend I have to attend tomorrow, right after school lets out. I get up, go into the bathroom and try to calm myself down. When I look in the mirror, I see the face of the evil teddy bear staring back at me and cry even harder.

The next morning, I just throw on a hoodie and pray that the T-shirt brings me luck. I walk past the ghost of Stupid Boy in the hallway, his obnoxiously blue eyes look right through me as if I’m the one who’s dead, but I don’t give a fuck. I find a desk by the window, take a seat, and stare out at the front lawn, at my favorite tree for the last time. I look down at my test, hold my breath, and pray for a solid D-.

It is February 2013. I sit in my Freshman year Political Science college course. I prepare to take the second test of the semester. Even though last week, the professor made a point to let everyone know my test grade was the highest in the class, I’m hoping to score even higher. You see, this time, there’s an evil teddy bear on my shirt and I’m hoping it will bring me some luck. A Strange Boy with light brown eyes walks in late, sits next to me, taps me on the shoulder and says,

“Hey Smart Girl, I like your shirt.”

I smile, think of a Stupid Boy I used to know and get to work.

Tonight marks the last week of January 2020. My closet is full, but my bed is empty; a result of choices, regret, and time. My chest feels hollow, but I can’t help but smile, because after everything I have lost, these memories and this T-shirt are still mine.

So, here’s to the Stupid Boy from high school whose Shirt I still sleep in. I hope I dream of you tonight.