Embarrassing Childhood Crush Stories

When you’re very young and in love, you don’t have it quite figured out yet. More than likely, you’ve done something absurd to hopefully attract your elementary or middle school crush. I asked a few of my friends what their most notable childhood crush experience was, andĀ found I wasn’t alone in being a complete weirdo as a tween.


My Story

When I was 14 years old, I had a crush on my neighbor who lived across the street. She always sat out on her stoop, texting on her pink motorola razr v3. (Probably in t9 predictive text mode.) She had a scene girl fringe haircut, so I assumed she liked emo and pop punk music. It was a pretty stupid assumption because it was 2007 and every girl had that haircut.

I was a shy kid back then, so I was too afraid to go up and talk to her. Instead I decided to point my speakers out the window and blast Taking Back Sunday and Fall Out Boy for days on end, hoping she’d notice me because we liked the same music.

Her family moved a few months later. I never ended up speaking to her, but I feel that trying to get her attention was a big part of me becoming a soft alt kid and listening to depressed teenage girl music for the rest of my life.



It was 1st or 2nd grade and I was at recess awkwardly hanging out with my crush. The place they had us lineup at before we headed back inside had some stairs nearby.
They looked like this. Except the top and bottom rails were closer together.

Well one of the other guys there stuck his head in between the rails. I don’t remember exactly what was said but she was very impressed. So I did the only logical thing and also stuck my head between the rails. The problem is I was a lot bigger than the kid who did it before and got stuck. They went to get a teacher for help but I was stuck real good. After about 5 minutes the teacher went in to get some lube from a custodian. Thankfully I managed to got unstuck before they came back, but I never lived that down. I remember trying to talk to them in middle school and make a move and the first thing they did was bring that up.



When I was 13, I was playing footsie with a girl I sat next to on a bus ride for a field trip. I was getting all excited that this cute girl was actually paying attention to me, and doing it slyly….she never stopped talking to her friends, but any time I pushed my foot against hers, she’d push back just as hard. Never even moved her body away from mine. It was like, our own little secret crush.

Then we got to our destination and she stood up and started to leave. But I was still playing footsie with her somehow.

Turns out I had been rubbing up against the leg of the seat the entire time.



In 9th grade I asked my dad to get me a guitar for christmas so I could learn the songs that my crush had on her MySpace. I learned Hey There Delilah and I was so obsessed with her that I replaced Delilah with her name. SMH.



When I was in 3rd grade, during class, I wrote “Adidas” on a small piece of paper, and then wrote:


And then I gave it to this guy I was working on a project with at the time, and told him to give it to this girl I liked. He said “okay”, and then I watched him get up and take the piece of paper directly to the teacher and tell on me. I then got suspended for sexual harassment.


If you’ve done something to attract someone back in the day that you still cringe at, don’t worry because you aren’t alone at all. But if you’re like, 24, then maybe it might be a good time to reevaluate your dating strategies.

Have an embarrassing story you’d like to share? Text me or send me an email at kennethwoo11@gmail.com

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