My First Boyfriend Messaged Me 25 Years Later

18-Year-Old Me was devastated.

Jenn M. Wilson
Published in
6 min readApr 7, 2021

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Photo by Hunter Newton on Unsplash

What are the major milestones in our lives?

Learning to walk.

Getting a driver’s license.

Graduating high school.

Moving out on your own.

Getting married.

Having a child.

No one ever mentions an event that forms your future relationships: your first love.

Or, more specifically, the heartbreak that comes with first love.

It was a classic tale of teen romance. Jeff was two years older, lived in a redneck town a few hours away, and came to my high school for a volleyball game.

I was 14, only one of three somewhat ethnic kids in my high school with ultra-religious parents and perfect grades.

Tale as old as time.

In a world lacking internet and cell phones, but with strict parents who wouldn’t even let me wear shorts, our only form of communication was by the written word. Since my mother read all my mail, Jeff sent his letters to my friend’s house. Eventually, I got my own phone line, but the written letters remained. While I was beating myself up for my imperfections, Jeff told me I was his “parents’ wet dream of a…

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Jenn M. Wilson
Jenn M. Wilson

Written by Jenn M. Wilson

My midlife crisis and adventures along the way. I write because in real life my humor is allegedly too sarcastic and inappropriate. MediumNinjaGirl@gmail.com

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