This Week’s Most Unhinged (and Weirdly Useful) AI Prompts (week 1)
From pirate lawyers to lovesick toasters, we tested the week’s wildest ChatGPT prompts so you don’t have to. Spoiler: you’ll want to try them anyway.
5/19/20252 min read


Welcome to Prompt Roulette, where we fling absurd requests at ChatGPT and document what happens.
Some were helpful.
Some were hilarious.
One of them made me emotional about bread.
Here’s what made the cut this week:
🔥 1. The Surprisingly Useful Prompt
Prompt:
“Act as a productivity coach who has zero chill. Plan my week like you’re preparing me for battle.”
Result:
“Rise at 5:47 AM. Hydrate with two fists of water. No phone until the war horn (calendar alert) sounds at 6:30. Monday is for DEEP WORK. Block all distractions. If Karen from HR tries to chat, deploy ‘Can’t Talk – Mission Critical’ script.”
Best For:
People who want to get things done and feel like they're leading a Viking raid.
💘 2. The Emotionally Confused Prompt
Prompt:
“Write a love letter from a toaster to a bagel.”
Result:
“My dearest Bagel,
From the moment you nestled inside me, I felt warmth in my coils I’d never known. You complete my cycles. You are my golden crisp muse.”
“I burn for you. Literally.”
Best For:
People who are single, romantic, and a little unhinged before caffeine.
🧠 3. The ‘Wait… That Worked?’ Prompt
Prompt:
“Summarize this legal document like you’re a pirate explaining it to children.”
Result (actual summary line):
“Arrr, ye be entitled to treasure (aka payment) if ye swab the decks (aka fulfill your contractual duties). But if ye abandon ship early, ye’ll face the wrath of the financial kraken (aka termination clause).”
Best For:
Anyone who reads legal stuff and instantly flatlines.
🍽️ 4. The ‘I Might Actually Use This’ Prompt
Prompt:
“Create a weekly meal plan for someone who hates cooking, is lazy, and forgets to shop.”
Result:
Monday: Pasta with canned sauce.
Tuesday: Leftover pasta.
Wednesday: Toast with whatever you find in the fridge.
Thursday: Frozen pizza.
Friday: Order takeout, lie to yourself.
Saturday: Cereal.
Sunday: Panic grocery run.
Best For:
People living that beautifully dysfunctional kitchen life.
🎤 5. The “I Didn’t Ask for That, But Thanks” Prompt
Prompt:
“Write a rap battle between my brain and my anxiety.”
Result (actual bars):
Brain:
“I keep it logical, factual, always on task—
You bring sweaty palms and existential asks.”
Anxiety:
“You plan. I panic. It’s the perfect duet—
I spike cortisol like it’s the Internet.”
Best For:
Anyone whose inner dialogue sounds like a Spotify cypher at 2am.
✅ Final Thoughts
AI doesn’t just help you work smarter — it also helps you spiral funnier.
Try these prompts. Or better yet, send us yours and we’ll let ChatGPT embarrass itself for your amusement.
👉 Want more like this? We do this every week.
Visit shamelessplugs.me for a fresh batch of AI-generated brilliance (and occasional nonsense).
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