An Experiment in Hemmingway

Updated: Jan 8

For people who struggle to read white on black, read this on Medium instead,

A few months ago I got bored and decided to play around in Hemmingway Editor to see how pretentious I could make a piece of writing, and what the highest reading grade it detects is.

I succeeded in having it jump to a postgraduate level; most of it came from long, run-on sentences and chunky paragraphs larger than a “chonky boy” cat on the brink of heart failure. Word choices were a secondary factor.

I decided to play with the same story but see if I could get it down to a 0 — so perfectly dumbed down, but still understandable, that Hemmingway dubbed it kindergarten-friendly.

I’d like to share both stories with you, just for fun. Be warned, the first one’s a real bitch to get through when those paragraphs balloon.


The atrocious quality of this vibrating sailboat postulated across my perineum. Slathered in the blood of my enemies, I metaphorically imbibe it copiously. Shredding every last ounce of flesh upon these dusty mortal coils I shall sail away into a deep and cavernous oceanic space until the night envelops me in its unforgiving, bitter cold.

The foul stench of rotting flesh pierced these old and worn nostrils as we passed beyond the horizon and into the unknown lands owned by the Dancing Pirates of the ship Bad Fortune. Aye, there’s the rub — it’s their typical Sunday night feast of their dead, usually stored deep in the bowels of their intrinsically evil wooden cavern they dare refer to as a ship.

By this point I was desperate to staunch the flow of thick, overwhelming rot so I did the only thing my brain could fathom and ripped the cloth from my terribly tied tourniquet, unleashing a river of poisoned, red, royal blood and filling the bottom of my rickety sailboat.

Tonight is the night I perish, I thought bitterly. Tonight my life ends and tomorrow they find my body, masked in a pool of my own blood, and the poison I injected that I could activate if ever I was caught by my enemies far across the sea. One pill, Johnston, is what Galen said. One pill and the poison becomes fatal as the wound that left my poor, trusty sailboat in a state far beyond repair, far beyond desire, far beyond what my precious splintered companion deserved. I don’t think I’ve ever been more sorry than I was that night, the night I degraded and defiled the only object that exists in this physical plain that I’ve ever loved. I’m sorry, my sailboat, I cry this to thee now, that I pledge in my next life I will never harm you again, nor think unsightly thoughts of impurity involving self-pleasuring while seated in your warmth upon the silent sea, thinking of the women I will never get to have, to penetrate, to taste again. Then the guilt poured in, as those poor, unsuspecting women were my final thought, and no, that’s not why I felt guilty, the guilt pierced me because my last brainwave held no trace of my faithful sailboat companion whatsoever, and I am an evil man who deserves nothing but to burn in the darkest, most fiery pits of whatever nasty underworld lurks beneath the crust of the planet I was sent to on my mission to rid this universe of the scourge of humanity.

When I get there, I hope they have pie, the human food I detest the most and deserve to consume every day for the rest of my burning eternity down in the darkest reaches of the longest fingers upon the most polluted shore of the devil’s not-so-humble abode. It should be filled with the sweetest berries which have no taste other than this ongoing filthy tartness that I will never scrub out of my fleshy tongue, my rotting teeth and the pores in my skin, which as it is, is riddled with open sores and oozing infection. I wonder if these festering wounds would have killed me before the poison, or before the leg which when freed from the safety net of the tourniquet, snapped clean off in a sickening melody in the frigid night air.

Lowest Grade Possible: Grade 0

My sailboat was being bad and made my butt jiggle. I was covered in bad blood. I drank in the jiggles.

All my skin is peeling. I will sail away. Past the sky line into a mystery on a cold night. I will get lost.

I smelled dead people as I sailed. This is where the Dancing Pirates live. They lived on a ship called Bad Fortune. There’s the catch. It’s Sunday night dinner. They eat dead people. They store the dead on the bottom floor of the ship. Their ship is yucky.

I wanted to stop. I took the bandage from my sore leg. I started bleeding. My blood is dirty with poison in it. It filled the bottom of the boat.

I thought I’d die that night. Tomorrow they’d find my body in a pool of blood.

Poison blood for if my enemies caught me. If I took one pill the poison would kill me.

My boat wasn’t good enough to sail this far. I’m sorry I tried to. I loved that boat.

I think that in my next life I’ll treat the boat better. I feel bad that I masturbated in the boat. I thought of women I’ll never have.

I felt guilty when I thought of the women. I felt guilty because I didn’t think about my boat when I died. I should go to hell.

I hate pie, so they should feed it to me forever. Down there in hell. It should be berry pie because I hate berries.

I’ll never get the smell of berries away. It will go into my cuts. I wonder if my cuts would have killed me before my leg fell off.

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