The Birth of the Cynical Romantic
Fifth grade. The year my love life became a running sitcom, complete with an audience, punchlines, and the occasional humiliation. If only I had realized then that this was just the beginning of a much longer, cringe-worthy romantic saga.
This is the first of two defining fifth-grade “love” experiences—events that should have been a warning sign for the heartbreak, melodrama, and confusion that would shape The Cynical Romantic I am today.
My First Breakup (From a Relationship I Didn’t Know I Was In)
It began with a letter. Well, more of a shredded, scribbled-on, rage-fueled note that appeared under a book on my desk one afternoon.
It was a breakup letter.
I was stunned. Confused. Baffled. Mostly because I had no idea I even had a girlfriend, let alone that I had broken up with her.
The letter, though mostly redacted in an impressively aggressive manner, left one clear message:
"I hope she breaks your stupid heart like you broke mine!!!!!!!!!!"
No signature. Not that she hadn’t signed it—she had—but then angrily scratched it out with enough force to nearly tear through the paper. The scene played out in classic fifth-grade fashion:
I read the letter, mouth agape, looking like a startled goldfish.
The boys sitting around me, peering over my shoulder, erupted into laughter.
The girls didn’t laugh. Oh no, they just stared—a silent, unified force of judgment and impending vengeance.
It would take years before I solved the mystery of my accidental heartbreak.
Fast forward to high school graduation—one of my oldest friends, who had known me since Kindergarten, finally confessed that she was the author. We laughed, we hugged (our first ever), and she admitted she couldn’t remember all she wrote—except for how passionately she X’d out most of it.
And honestly? Looking back, it was the best breakup I would ever have.
My First Love Letter (A Shakespearean-Level Disaster)
Fifth grade also saw my first crush. The kind of innocent, overdramatic adoration that makes eleven-year-old boys go to extraordinary (and deeply embarrassing) lengths to impress a girl.
Naturally, I took the most logical and foolproof route: writing her a love letter.
At the time, I fancied myself something of a poet. (I was not.) But I had something even better—plagiarism.
Specifically, I borrowed lyrics from The Righteous Brothers' hit song "(You're My) Soul and My Heart’s Inspiration." My older brother listened to it, so clearly, it was cool.
This masterpiece of fifth-grade romance began with:
Girl, how can I live through this
Let you walk away
When you’re all I wake up for each day, baby
And it got worse.
I filled a page and a half with poetic (and borderline desperate) declarations of her beauty, her “raven-black hair”, and her “infectious laugh.” (I had heard the word infectious in a Cary Grant movie and looked it up. Very classy, right?)
I wrapped it up with my grand finale:
Baby, I can’t make it without you
If you say no, it will kill me, I swear it.
[Girl’s Name], I just can’t bear it.
Superb edit, right? “If you go” just didn’t have the same dramatic weight as “If you say no.”
For added effect, I included two big checkboxes:
☐ YES
☐ NO
Classic. Foolproof.
I signed it in newly-learned cursive (because printing was too casual for a declaration of love).
Everything was perfect. The only thing left was the delivery.
The Love Letter That Never Reached Its Destination
Since I was a genius in stealth tactics (spoiler: I was not), I recruited my twin sister to deliver the letter on my behalf. The plan? Sneak it onto my crush’s desk, unnoticed.
My sister, however, did not grasp the concept of subtlety.
She walked straight up, plopped it onto the girl’s desk, and walked away.
When my crush returned to her seat, she did not secretly unfold it with bated breath, as I had envisioned. Instead, she picked it up, looked around confused, and said out loud:
"Whose is this? Did someone drop it?"
And then… disaster.
My fifth-grade teacher, Mr. Walters, walked over, took the note, and—grinning—decided to read it aloud.
With the gravitas of a Shakespearean actor, he performed my love letter as if he were delivering the emotional climax of a soap opera.
My classmates howled with laughter. I desperately tried to disappear.
And then, something unexpected happened.
Instead of ridiculing it, Mr. Walters declared my letter well-written, funny, and, dare he say… “inspired?” That last reference delighted about half the class who caught the pun.
He never revealed who wrote it or who it was for. But a few heads turned in my direction, and I had the sinking feeling that my secret was not so secret anymore.
The Lesson? Humiliation is Inevitable in Love.
That day, I learned two critical lessons about romance:
If you don’t know you’re in a relationship, you’re still responsible for the breakup.
If you write a love letter, assume it will be performed publicly.
And so began my journey—a tale of heartbreak, teenage melodrama, and Shakespearean-level embarrassment. But if fifth grade taught me anything, it was this:
If at first you don’t succeed in love… just wait until high school, where the stakes are higher, and the humiliations come with a soundtrack.
Oh, and if you haven’t already? Go listen to "(You’re My) Soul and My Heart’s Inspiration." Trust me—it’s a classic.
Also, in case you’re wondering how I remembered the exact details of that love letter over thirty years later—well, Mr. Walters handed it back to me after school that day.
And yes, I kept it. Because, after all, who would throw away something written by the next Shakespeare?