2 minute read

I’ve spent the better part of the last few years in a slightly surreal relationship—collaborating closely with an AI whose main ambition seems to be to sound exactly like…me. Or you. Or at least some convincingly clever, humanlike version of a copywriter who occasionally makes a good joke.

Let me save you some suspense: it wasn’t always pretty.

Attack of the Bland AI Copy! Vintage Poster

Common Mistakes When Prompting AI for Humor

First, let’s cover what doesn’t work. Asking your AI tool to “be funny” or “sound human” without context is like asking your cat to “act doglike.” Sure, it might chase a ball briefly, but it’s probably by accident.

If you’ve ever prompted your AI writing tool with something like:

“Write something funny about Zoom meetings.”

You might have gotten back something painfully generic, like:

“Zoom meetings: pajamas below, professionalism above!”

Cute? Maybe. Hilarious? Absolutely not.

The issue: AI defaults to surface-level humor because it doesn’t inherently understand nuance or context.

Effective Strategies for Prompting AI Humor (With Examples)

What I’ve found most effective is guiding the AI with personas and detailed context. Instead of vague prompting, say something like:

“Imagine you’re a sarcastic tech blogger who’s suffered through 6 hours of Zoom meetings today. Write a tweet reflecting your state of mind.”

The result?

“Spent 6 hours today proving humans can endure anything, even endless Zoom calls. Scientists, take notes.”

Not perfect, but suddenly there’s personality. That’s because you’re giving AI context it can latch onto—attitude, scenario, and a clear emotional starting point.

Surprising Lessons from My AI Copywriting Journey

Here are two unexpected insights I’ve discovered:

  1. Balanced Tone Instructions: If you give AI just one adjective for tone (“funny,” “friendly,” “smart”), it caricatures itself horribly—think Disneyland-level cheerfulness or exaggerated enthusiasm. The fix: use balanced, nuanced instructions like “clever but casual” or “professional but approachable.”

  2. Few-Shot Learning Magic: Showing AI just two examples of your preferred humor or style dramatically improves the quality. It quickly learns to mimic your rhythm, humor cadence, and word choice better than any generic instruction.

How My AI Prompting Has Improved

Early on, my prompts looked like:

“Give me a clever tagline for a coffee brand.”

Now, my prompts are layered:

“You’re an over-caffeinated copywriter at 2 AM. Write a punchy, slightly self-deprecating tagline for a coffee brand targeting fellow late-night hustlers.”

And I often add examples:

“Like ‘Coffee: the official sponsor of last-minute miracles.’”

This small shift—making my instructions narrative-driven and context-rich—turned my AI sessions from frustrating randomness into genuine creative collaboration.

Why Mastering AI Writing Matters

Ultimately, creativity is a deeply human act. Using AI effectively isn’t about replacing that human element but enhancing it. The best AI writing emerges when we stop expecting it to magically deliver brilliance from thin air. Instead, we learn to see it as an insanely quick, tireless junior partner who needs clear guidance and occasional patience.

So next time you sit down to craft a prompt, remember this: your AI is only as funny, clever, or human as the story you help it tell.

Now, if you’ll excuse me, my robot intern is reminding me we have another Zoom meeting in five minutes. Wish us luck.

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