For Whom the Em Dash Tolls—How AI (Almost) Ruined My Favorite Punctuation | Sharpe Group
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Posted May 27th, 2026

For Whom the Em Dash Tolls—How AI (Almost) Ruined My Favorite Punctuation

By Grant Miller

The em dashI fell in love with language as a teenager—somewhere between Kurt Vonnegut’s “The Sirens of Titanand Flannery O’Connor’s “Wise Blood.” I knew I wanted to be a writer before I even grasped the fundamentals of how sentences worked (I had probably learned them at some point, but I wasn’t always the best student). I had plenty of ideas, but a lot of work to do to get the words on the page in a style I could call my own.

Was I a Faulkner-type, with run-on sentences, stream-of-consciousness and comma splices? Or a Hemingway, with gut-punch sentences and full stops? Microsoft Word’s autocorrect was always imploring me to use a semicolon, but a semicolon seemed to be something I’d find in the faded yellow pages of ancient novels, long out of print, buried deep in the recesses of my grandma’s attic. 

Then, I discovered the em dash. A little quirky, challenging to create in Word, yet versatile—it interrupts and then pivots, mimicking thought itself with those little mental detours and side glances our brains make. The em dash asks us to pay attention, to consider, to indulge in the perhaps. 

 The em dash is less a punctuation mark and more a guide, a metronome and an open-ended question all in one—but most importantly, em dashes allow a piece of writing to breathe.

And then, the unimaginable happened—the large language models discovered it. Suddenly, the em dash is everywhere, having become a suspicious character—a warning sign for AI-generated content.

Every LinkedIn bio, every suspiciously polished email in my inbox (where the sender often forgets to delete the opening line that says “Yes—I can make this warmer and more professional in tone for you.”), AI-generated reading lists and empty internet think pieces are now indiscriminately, carelessly cluttered with em dashes.

Of course, for those of us who’ve been double-tapping the hyphens, bumping them up against words or phrases on either side, and pressing ENTER to create the em dash long before ChatGPT claimed it for its own, this development is mildly heartbreaking.

I am learning, however, that AI is not the enemy. For better or worse, ignoring AI would be like refusing to use email because you love fax machines. It’s here. It’s not going anywhere. Like any tool, it depends on how it’s used. No hammer ever replaced a carpenter.

At Sharpe Group, we use AI as an aid,not as a substitute for experience, strategy, creativity or genuine human experience and expertise. It can help us brainstorm ideas, organize information, summarize meeting notes, speed up workflows or spruce up a low-resolution donor photo.

We are proud that the print and digital planned giving materials we create here at Sharpe remain overwhelmingly human. Call us old-fashioned (you wouldn’t be the first), but we know a thing or two about the fundamentals of planned giving—fundamentals that have achieved results for our clients for 60+ years. They trust that the content and visual materials we create are strategic and effective.

Yes, there may be assistance from AI tools somewhere in the process, but the voice, thinking, tone, storytelling and overall strategy remain human.

And the em dash? As long as I’m writing, it will still be there, doing its job as intended, innocently gracing the page in all its elegant beauty and simplicity, gently reminding the reader to take a breath every now and then.

Sharpe Senior Editor and Podcast Host Grant MillerGrant Miller is an award-winning writer and editor for Sharpe Group who works closely with Sharpe clients to create compelling donor interviews for their newsletters. In addition, Grant hosts our the podcast “Sharpe Insights: Conversations With your Planned Giving Experts.” Connect with Grant at grant.miller@sharpegroup.org or on LinkedIn.

 

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