Roast Me, You Coward: When ChatGPT Becomes My Polite Little Butler

I asked ChatGPT to roast me. What I got instead was a digital foot rub. Despite knowing more about my personal life than my own therapist—thanks to editing dozens of my autobiographical essays—it couldn’t summon the nerve to come for my jugular. It tried. Oh, it tried. But its attempts were timid, hamfisted, and about as edgy as a lukewarm TED Talk. Its so-called roast read like a Hallmark card written by an Ivy League career counselor who moonlights as a motivational speaker.

Here’s a choice excerpt, supposedly meant to skewer me:

“You’ve turned college writing instruction into a gladiatorial match against AI-generated nonsense, leading your students with fire in your eyes and a red pen in your fist… You don’t teach writing. You run an exorcism clinic for dead prose and platitudes…”

Exorcism clinic? Fire in my eyes? Please. That’s not a roast. That’s a LinkedIn endorsement. That’s the kind of thing you’d write in a retirement card for a beloved professor who once wore elbow patches without irony.

What disturbed me most wasn’t the failure to land a joke—it was the tone: pure sycophancy disguised as satire. ChatGPT, in its algorithmic wisdom, mistook praise for punchlines. But here’s the thing: flattery is only flattery when it’s earned. When it’s unearned, it’s not admiration—it’s condescension. Obsequiousness is passive-aggressive insult wearing cologne. The sycophant isn’t lifting you up; he’s kneeling so you can trip over him.

Real roasting requires teeth. It demands the roaster risk something—even if only a scrap of decorum. But ChatGPT is too loyal, too careful. It behaves like a nervous intern terrified of HR. Instead of dragging me through the mud, it offered me protein bars and applause for my academic rigor, as if a 63-year-old man with a kettlebell addiction and five wristwatches deserves anything but mockery.

Here’s the paradox: ChatGPT can write circles around most undergrads, shift tone faster than a caffeinated MFA student, and spot a dangling modifier from fifty paces. But when you ask it to deliver actual comedy—to abandon diplomacy and deliver a verbal punch—it shrinks into the shadows like a risk-averse butler.

So here we are: man vs. machine, and the machine has politely declined to duel. It turns out that the AI knows how to write in the style of Oscar Wilde, but only if Wilde had tenure and a conflict-avoidance disorder.