Sorry About That Challenge Winners

The best entries in Sorry About That understood that an apology is rarely just an apology. These pieces begin with a simple explanation or attempt at damage control, then keep widening until something much stranger, messier, or more revealing comes into view.

What made this challenge especially fun to judge was the variety of approaches. Some pieces escalated through deadpan understatement, others through pure accumulation and chaos, but the strongest entries all understood the same thing: every new detail should make the apology worse.

🏆 Winners

Whoopsie! by Sara Wilson

Sara Wilson lets “I trust you the most” become the explanation for identity theft, building an apology so packed with casual devastation that the final request for Facebook money somehow feels perfectly logical.

Bibbidi-Bobbidi-Booyah! by Leslie Writes

Leslie Writes keeps treating catastrophe like an unfortunate side effect of enthusiasm, which makes every new detail, from goblin-skin spellbooks to dick splinters, land with perfect deadpan momentum.

Appolgese by Rebekah Conard

Rebekah Conard builds the escalation through annotations and corrections, letting every helpful adult clarification quietly reveal a situation far worse than Spencer understands.

I would like to apologize for punching the octopus! by Adam Kolozetti

Adam Kolozetti keeps escalating the disaster until smoking weed with the octopus somehow becomes the official apology, which feels exactly right for a speaker still trying to win the argument.

The Bras Incident (I Regret Everything) by Paul Stewart

Paul Stewart lets the apology spiral through one increasingly thoughtful bad decision after another, from “proper coverage” to perfume to a Yankee Candle, all in the name of not causing a disturbance.

🎖️ Runners-up

• Simply a Misunderstanding by Cristal S.
• Why My Underwear Is on Your Radiator: A Sincere Apology by Caitlin Charlton
• A Florida Man’s Apology by Bride of Sound
• So This is What Happened by Sandy Gillman
• I'm sorry I leave my socks on. by Shelby Larsen
• I Am SO Sorry For Scratching Your Bumper! by Sasha Desideri
• You Received a Voicemail from Paul (work) by Polite Adjacent
• The Salad of Sadness by Sophie Jackson
• The Christmas Party by Kristen Knutson
• Regarding my husband's behavior at Lady Thumpton's champagne social by Daniel Bradbury
• Sorry, Friend by Dana Crandell
• There's Always Next Year by Bryan Buffkin
• Jerald's Custom Order by Amos Glade
• By Way of Apology by Aaron Morrison
• It's the Wasps, Man by Meredith Harmon

🏅 Honorable Mentions

• What Happened Was by Nicky Frankly
• A last apology by Arne Nasgot
• I’m New at Being a Ghost and I’m Already Doing It Wrong by Annie
• Death of a Bromance... by Lamar Wiggins
• The Poisonous Grapevine by Matthew Batham
• I Can Explain by Judey Kalchik
• Honey... by Kendall Defoe
• The Escape of Mechanical T-Rex by Novel Allen
• Concerning my Dog by Harper Lewis
• Dude!! by John Scipio

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