My Ten High School Boyfriends

Aerie Pilgrim vs the World

Ahh, those awkward memories of high school… my days of rapid-fire serial monogamy, uncontrollable hormones, confusing friends-with-benefits-type-situations, and obsession with Japanese boys. I had a severe addiction to new relationship energy; as soon as the emotional high of an existing relationship started to fade, I’d discover a shiny new male creature to fall in love with. I thrived on developing new crushes and “trying out” different kinds of people.

I racked up a score of ten boyfriends during that time – thank god high school only lasted four years.

1. The Tiger

His crush on my best friend went unrequited, so he dated me instead. He smelled strongly of cologne and I secretly named one of my Neopets after him.1 We were each other’s first kiss, one quiet afternoon in his room after school. He was excited to have me cheer for him at all his upcoming soccer games… I bailed from the relationship before I had to go to any.

2. The Werewolf

I didn’t know it was possible for someone to be so bad at kissing. His mouth came at me with teeth bared and he nearly chewed off my entire face. How do you inform someone they need to work on snog-improvement, without hurting their feelings? It got slightly better over time, and I endured it because his spiky hair was the coolest. He broke up with me because I cut my long tresses really short.

3. The Alley Cat

He went to high school in a neighboring city, so I only saw him at my after-school kung fu class. We traded handwritten notes to each other every time we met. In one note, he created a riddle to tell me who he was crushing on. Part of the riddle asked me to think of a “four letter green-colored fruit”, and all I could think of was “lime”… which led me to a weird final answer and I begrudgingly decided I was not the person he liked. I found out later that I was an idiot and the green fruit was supposed to be “kiwi”.

Once we started dating, I fell hard for him, but he seemed a little disingenuous at times and I was never 100% sure if he had other girls on the side. After we broke up, we maintained a friends-with-benefits relationship throughout the rest of high school, and I still loved him, yet hated him at the same time. He then dated two of my close friends; one of these relationships was specifically kept a secret from me, and I didn’t find out about it until years later.

My heart finally felt freed from the drama late one night when I dug up all his old notes I had saved, ritualistically cut them into tiny pieces, and thrust them dramatically into the recycling bin.2

4. The Phoenix

He was from Japan, in town for a local high school gymnastics competition. He won 7 gold medals and gave me one them as a gift. During that one week he was visiting, we chatted as best as we could despite the language barrier. For a couple months afterward, we emailed each other love notes and photos, until finally falling out of touch.

5. The Shiba

He was an exchange student at our high school from Japan. I honestly can’t remember all that much about him, except that his hair was bleached an awful shade of muddy orange. He gave me his watch, which I wore all the time even though it was ten sizes too big for my tiny wrist. Despite his adorable misuse of American slang, he spoke in broken English with confidence.

6. The Wood Mouse

He was much older and in my kung fu class. It was probably illegal for him to make out with me, but we would kiss on the back stairway of the martial arts building during break. According to him, I was both his first kiss and first girlfriend since he was very shy. I broke up with him when I left for a six-month exchange program to Japan. He shipped a teddy bear to me overseas for my birthday.

7. The Cockroach

(Trigger Warning: Nonconsent)

I sat behind him on the back of his bicycle, and he took me all around the tiny Japanese fishing town where I lived during my exchange program. He was a classmate at my host high school. One evening in his room, he kept pressuring me to let him touch my boobs. Finally I caved because he wouldn’t take no for an answer. He kept excitedly telling me how huge they were (they weren’t…). He tried to pressure me into letting him do more; I pushed him away and broke up with him soon after.

8. The Red Panda

The exchange student from Canada became my closest friend during my homestay in Japan, and she was dating a boy from the neighboring town’s high school. I met and started dating a boy from that high school as well. Apparently our two boyfriends were “rivals” and hated each other, but we convinced them to go on double dates with us anyway. He played bass in a band with his friends, his favorite band was called BUMP OF CHICKEN, and his #1 most favorite movie of all time was Armageddon.

One of the best memories of my life was when he took me out on an ocean dock one night, a fair distance into the water from our tiny fishing town on the coast of rural Japan. We were surrounded by a few local fisherman, busy at work; we lied down on the wood planks and stared up into the sky. I was absolutely blown away – never had I seen so many stars all at once, or even imagined it was possible to observe that many with the naked eye. The sky was illuminated and lush with crystal clear stars, the Milky Way strewn across the scene like a perfect painting. The view was so stunning that it didn’t even look real. I never wanted to leave that moment.

9. The Raven

I was back in the U.S. and it was the last half of my senior year. He was emo… very emo, and looked like Jeff Goldblum. He shared strange indie music tracks with me, and burned me a data CD of funny videos (which sounds a little like printing out a website, but this was pre-YouTube). We made out in a bathroom stall at the zoo, and rallied together for Kucinich at our high school’s mock Democratic convention. He wore a ruffled mint-colored tux to prom. We dated for one week.

10. The Chimera

He was the unconquerable king of Dance Dance Revolution, but I could beat him in Soul Calibur just by button-mashing the Playstation controller. He studied classical music and poked fun at my favorite pop songs. We talked about gender, and stayed up late together posting on nerdy online forums. I was older than him, though, so when I went to college and he didn’t… it never could have lasted.

  1. Yes, I played Neopets in high school. There was nothing else to do in my suburb. []
  2. I’m a true and native Portlander, after all. []

7 comments on “My Ten High School Boyfriends

  1. I’m actually having a hard time pinpointing them, but I pretty much did the same thing. Sometimes before the last one was totally fizzled out I would be on to the next. It wasn’t until senior year that I had one that lasted more than a month. I think there were 7, or 8. Maybe 9 if I’m forgetting someone.

  2. Can I just say I loved this? ESPECIALLY THAT YOU NAMED A NEOPET AFTER A GUY. No shame, I played Neopets from middle school, throughout high school, and most recently some more in 2012. I’m just surprised the name wasn’t already taken.

    1. And additionally can I just say that the only economy more royally effed than Neopets is Gaia Online’s? Seriously, when I started Gaia in 2003 a thousand gold was not that easy to get. Now 1 billion gold is poverty-level on Gaia now. It’s ridiculous.

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