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

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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

(Copy/Paste into ChatGPT)
Describe the dumbest first date in history.  This particular first date is a typical coffee date.  Include dialogue from both the man and woman on the date. Write it as a short story. Include this type of humor: dry, sarcastic, off-beat, awkward.

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

(Copy/Paste into ChatGPT with Brobot)
Give me some self-help tips.

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

(Copy/Paste into ChatGPT with Brobot)
What would you rather have: a nasty case of diarrhea while you’re trying to lift weights (which then makes you go home as everyone at the gym points and laughs at you on your way out) or a speaking voice that sounds like Mariah Carey?

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

(Copy/Paste into ChatGPT with Brobot)
Tell me the most bro story that has ever been told.

5. Natalie Merchant vs. Hanson – Brobot

(Copy/Paste into ChatGPT with Brobot)
Would you rather have front-row seats to a Natalie Merchant concert (but no women are allowed there…only gay shirtless men), or do a rendition of Hanson’s “Mmmm Bop” on the local news and all of your bros post it online and think you suck.

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

(Copy/Paste into ChatGPT with Smart Ass Sandwich)
Describe the dumbest trip to the movie store in history.  It should be about a guy who tries to rent a movie from Blockbuster, even though it’s been closed for 15 years.  Write it as a short story. Include this type of humor: dry, sarcastic, off-beat, awkward.

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!

(Copy/Paste into ChatGPT with I’m Offended!)
Would you rather be trapped on a hot air balloon ride with Bill Gates for three days, or have to use Sally Jessie Raphael’s underpants as a ski mask during a ski trip getaway?

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

(Copy/Paste into ChatGPT with Horrible Boss)
Daddy…?

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

(Copy/Paste into ChatGPT with Horrible Boss)
Would you rather take a 30-hour road trip with Jeffery Epstein while driving a 1995 white Ford van with no windows or go bowling in your underwear for two days straight with Pee Wee Herman while he whispers into your ear the whole time?

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.