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Kiss & Tell: Awkward Middle School Love Stories

We all have to start somewhere, and I guess that somewhere is middle school. Here is a roundup of THE most cringe-worthy middle school love “firsts”:



In something like seventh grade I was at a dance and some person threw a condom into the window from the street. It was the talk of the dance, and when I tried to contribute to the hype I asked, “Was it a boy condom or a girl condom?!” Everyone froze and a girl said, just pretend you didn’t hear it. #catholicschool #sheltered

In 5th grade my boyfriend got me these really pretty hoop earrings, but they were tiny and I have large earlobes. So, I gave them to my sister because she has small earlobes. He got really mad at me and thought I didn’t like them but I swear my earlobes were just too big!

I went on my first date with a guy named Redford! We went to the movies in downtown Bethesda, and in the movie I was too nervous to kiss him even though he leaned in for it a few times. I was so mad at myself and I promised myself that by the end of the night I would kiss him! We went to Starbucks after our movie, and I was going to kiss him as soon as we got to the door, but before we got there I was hit by a car that was screeching to a halt. That was my first and last date with Redford….

At the end of 6th grade I called my boyfriend’s house phone to break up with him but it went to voicemail so i broke up with him on the voicemail. His whole family probably heard it #heartbreaker

Had my first kiss at my 8th grade formal behind this makeshift curtain decoration in the hallway, only for it to be pulled open by a teacher right after we kissed. Then we had to walk back into the dance being escorted by the teacher, and when he tried to hold my hand she yelled at him. Bustedddd.


My first kiss was at our dance at camp while slow dancing with the boy I had a huge crush on..the counselors kept putting a giant balloon between us to break it up but we kept taking it out until they pulled us apart completely

This one time in 5th grade I wrote the boy I liked a love letter and stuck it in his backpack and he thought it was lunch money and so he gave it to the cafeteria ladies and they all read it and the whole faculty found out and it was awful.

The first time I ever kissed a boy our braces banged together and he cut my lip with his….. We never kissed again…

My first kiss was at a park and I was sitting next to my boyfriend on a bench when our two friends literally grabbed our heads and pushed them together… our lips did not touch but we both got a bump on our foreheads.. after being horrified for a few minutes we successfully kissed… 


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