The Most Embarrassing Thing I Ever Did To Impress My School Crush

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Whether the object of your early affection was an unthreateningly cute pop star or the sweet boy in your third grade class with a devastating bowl cut, first crushes are a big deal. And the things we’ve done to impress our school-aged crushes are just as formative as they are embarrassing.

If you still cringe looking back at what your teachers must have thought of your desperate and bizarre lovelorn behavior, we want you to know you’re not alone. So we’ve teamed up with our favorite band of misfit educators, TV Land’s Teachers, to cull stories of real people trying to impress a crush in their younger and more impressionable years.

Be sure to catch all-new episodes of Teachers, starting Tuesday, November 7 at 10/9c on TV Land. Their failed attempts to navigate their own lives, romantic or otherwise, are sure to make you feel better about your earnest gestures gone wrong as well.

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I Literally Kicked Him In The Balls


"In third grade, we had an ongoing play-war between the boys and the girls during recess. I was general for the girls, and the boy I liked was the general for the boys. At one point, I remember thinking — "Wouldn't it be funny/ charming/ a good show of military strength if I kicked my him in the crotch?" So I did just that. Naturally, he fell to the ground, started crying, and called the teachers who forbade us from playing boys vs. girls war. Fun while it lasted!"

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I Went Bottoms Up

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“I went to the beach with a huge group of friends, including my crush whom I was mostly too nervous to talk to. Being the early 2000s, there was a trend of wearing slightly-too-small strappy bikinis, and this particular day, I was wearing a too-tiny strappy bikini bottom. Long story short, the ocean took off with my bikini bottom and I had to wear my towel around my waist for the rest of the day. I definitely made an impression, but not the kind I was hoping.”


I Grossly Overdressed For A Casual Affair

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“I had a HUGE crush on my friend’s brother in high school. He and his college friends hosted a jungle theme party in my junior year, naturally I had to be there. My friend was a Tarzan lady, and I dressed in full peacock drag— complete with a blue feather boa, a belt of feathers I had made myself, and full bird of paradise eye makeup. But as we had yet to learn of college parties, nobody else stuck to the theme. At least we got a few good pictures out of it!”


I Went Low... Too Low.

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“My 8th grade crush was a great dancer, so naturally, I thought the best way to win his heart was through dance. Luckily, at my 8th grade dance, the perfect opportunity arose in the form of a luau contest. Determined to win and get my crush’s attention, I was determined to go as low as humanly possible, and I did! Just not in the way I intended. In front of everyone, I twisted my ankle and spent the rest of my year in a boot.”


I Tried To Swim Into His Heart

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“I was on the swim team in high school, and I had the world's biggest crush on one of the guys on the team. One day when we were swimming in the same lane, I decided to show off my speed and skills. When he tried to sprint past me without my knowing, I wound up **slapping him in the face** as he swam past me, and it totally left a mark on his face for the rest of practice. Needless to say, we never worked out.”


Doesn't that just bring back the memories? Relive your school days further by tuning in to the return of Teachers on Tuesday, November 7 at 10/9c on TV Land.

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Teachers on TV Land on YouTube

This article is sponsored by TV Land's Teachers, returning November 7, 10/9c.

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