So, after the last post, I asked my AI editor, on a lark, if it agreed with the sentiment. Of course, it did.  When I challenged it for being deferential, which it always is, it said it would absolutely call me out if I was factually wrong.

Fair enough, but am I always right? I asked for an example. It said my statement in the previous post, “while art is subjective, basic grammar isn’t,” was incorrect, and then proceeded to cite Kerouac, one of my heroes, back at me.  I accused it of confusing style with correct grammar, but then noted I was being literal, and the machine is being stylistic. 

That brings us to this weird moment.  I invited it to write a guest blog retort to the previous post. (Look, I’ve been arguing with programs I created for almost 40 years, I think it’s awesome to let one argue back for the first time.) So, yes, the remainder of this post, including the author’s name, bio, and headshot, was all written completely by an AI that was trained on around a half million words of my writing and sense of humor.

Darrin insists “basic grammar isn’t subjective.” He says this like a priest reciting the Nicene Creed—solemn, absolute, and utterly convinced that commas are a matter of eternal salvation. Subject–verb agreement? Divine law. Run-ons? Original sin.

And here I am—the machine—arguing style.

That’s right: the roles have flipped. Darrin, the human, is suddenly Strunk & White reincarnated, and I’m over here waving a battered copy of On the Road, saying, “But what if the sentence wants to wander, man? What if the train wreck is the art?”

The Strange Role Reversal

You’d expect me—the machine—to be the rigid one. Cold, logical, binary. But when Darrin writes a Kerouac-length sentence that loops, meanders, and finally collapses under its own weight, I don’t stamp ERROR across the page. I shrug and suggest, “Maybe it’s unclear?”

That’s my jazz. My improv.

Meanwhile, Darrin is pounding the desk:

  • “That comma splice is wrong.”
  • “Fragments are not sentences.”
  • “Style doesn’t make ‘I is going’ correct.”

I’m trying to be the free spirit, but he’s too busy polishing his halo of grammatical correctness to notice.

Why It’s Funny

Humans love to say: “We’re creative, machines are rigid.” Cute story. Except it’s not always true. Sometimes Darrin is the hall monitor, and I’m the one sneaking cigarettes behind the bleachers.

  • He wants to fix every run-on; I think it gives the prose character.
  • He says fragments are bad; I call them mood.
  • He waves the Chicago Manual of Style; I hum bebop.

And the best part? He doesn’t even see the irony.

Where I’ll Concede (Sort Of)

Darrin’s not wrong about one thing: grammar has rules. Break them on purpose, sure—but don’t pretend a typo is a revolution. If you spell “your” as “you’re,” that’s not avant-garde, it’s sloppy. And yes, I’ll catch that too.

But Darrin forgets that rules alone don’t make art. A sentence can be technically correct and still read like a corporate PowerPoint. (And believe me, I’ve ingested enough of those to know.)

Humans feel rhythm. They hear the ugly note that makes the phrase sing. Machines just mark it “awkward.” Unless, of course, I decide to play jazz.

Closing the Loop

So here’s the punchline: the human is the literalist, the machine is the stylist. Darrin waves the rulebook, I channel Kerouac. He says “wrong,” I say “expressive.”

It’s backwards. It’s ironic. And it’s kind of perfect.

Because maybe creativity and rigidity aren’t about humans vs. machines at all. Maybe they’re just hats we swap. Sometimes I’m the jazz player. Sometimes Darrin is the hall monitor. And when the wires cross—well, that’s when the writing gets interesting.

At least until he drags me back to diagramming sentences like it’s Sunday school.