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Funny Creative Things to Ask ChatGPT That You Haven’t Thought of Yet

by Nick Smith
Published: Last Updated on
Hacker Prompting ChatGPT

So you’re staring at your ChatGPT prompt window and asking yourself, “What are some funny things to ask ChatGPT? I’m incredibly bored, and I want this AI to entertain me.”

Lucky for you, I’m a standup comedian, so I would be happy to help you with this.

Actually, I’m not a comedian, but I do know how to make ChatGPT upset with me, so let’s just say I have this thing that you’re looking for down pat.

Word of warning, though: some of the prompts and responses in this post are obscene, stupid, or potentially offensive. If you’re not into that kind of thing, then… run away screaming.

One other thing you need to know: all of these prompts were made using GPT-4 and custom GPTs (which require GPT-4). What this means is I used the paid subscription to ChatGPT (ChatGPT Plus) for all of these prompts.

Does that mean these prompts will not work with the free version of ChatGPT? Of course not. They will still work with the free version, just not in the same way and not nearly as well.

I would recommend trying out the subscription if you haven’t already (no affiliation though). Or just see what happens when you run these prompts on the free version.

Anyway, you know what time it is. It’s time to join the circus we call RTP…

1. The Dumbest First Date in History is Also Funny – GPT-4

You can just run this prompt with GPT-4. No need to use a custom GPT. Run the rest of them (#2 – #9) with GPTs to get the best results. Don’t worry, I’ll provide links to all of them. And you can use all of them without any additional cost. All you need is ChatGPT Plus and an imagination.

2. Asking for Self-Help Tips from a Total Douchebag – Brobot

Want to chat with a total douchebag and ask him questions like this? Enter the Brobot GPT.

3. Gym or Voice Sabotage? That is the Question. – Brobot

4. The Most Bro Story That Has Ever Been Told – Brobot

5. Natalie Merchant vs. Hanson – Brobot

Try asking this question to ChatGPT without using Brobot, and I highly doubt it will be funny.

6. Asking for a Blockbuster Night – Smart Ass Sandwich

Experiment with this prompt with different GPTs. I used the Smart Ass Sandwich GPT, which is always a tasty choice.

7. Bill Gates & Underpants – I’m Offended!

Oh shit, she didn’t like this one! She doesn’t like anything. Don’t worry, you can offend her too. Use I’m Offended!

8. Daddy – Horrible Boss

Read this dialoge here.

Do you have a horrible boss? Even if you don’t, chatting with the Horrible Boss GPT is not a horrible idea. It’s a good one.

This conversation is long and stupid, but that’s okay.

9. Neither – Horrible Boss

Wrapping Up Funny Things to Ask ChatGPT

In conclusion, punking ChatGPT with a bit of humor and mischief has never been more thrilling. 

If you splurged on ChatGPT Plus and asked ChatGPT some of these funny things, I’m sure you were satisfied. Wait…you were, right?

Keep experimenting, keep laughing, and most importantly, keep asking those bizarre, outlandish questions. To yourself and an AI. In the grand circus of RTP, the spotlight is always on you. Actually, it’s always on me. Lucky for you, right?

Prompt the planet.

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