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

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 stand-up comedian, so I’d be happy to help you with this.

Actually, I’m not a comedian, but I do know how to make ChatGPT upset with me (or just plain confused), so let’s just say I’ve got this thing 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.

These funny prompts and responses were run with GPTs, various models in ChatGPT, and some in Venice.AI. I’ll detail that in the post, don’t worry.

But as an overall high-level rule of thumb, if you’re not going to use Venice or GPTs: If you have access to GPT-4.5, then use it for this use case. It’s the model that most easily produces creative outputs, such as short stories, poems, scripts, etc. And when it comes to comedy… creativity is vital.

If you don’t have access to GPT-4.5, then don’t worry. Just use what you’ve got. These will even work in Claude, Gemini, or whatever you want.

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

Prefer listening? Play the podcast version below! If not, just keep reading.

1. The Dumbest First Date in History is Also Funny – GPT-4.5

(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.

I ran this prompt with GPT-4.5. I tried it with GPT-4o, and it just wasn’t that good. Your mileage may vary, though.

2. Gym or Voice Sabotage? That is the Question – Bro Bot

(Copy/Paste into ChatGPT with Brobot)
What would you rather have: All of your bros point and laugh at you as you try to bench press 100 lbs but fail, or a speaking voice that sounds like Mariah Carey?  Answer in two paragraphs.

To get this type of response, be sure to use our very own Bro Bot GPT.  It’s free, even for non-subscribers. However, ChatGPT will restrict the number of messages if you aren’t a subscriber. That’s the case with all GPTs. If you’d like to test it with another GPT or without any GPTs, the result may also be good!

3. The Most Bro Story That Has Ever Been Told – Bro Bot

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

Again, you don’t necessarily need to run this with Bro Bot, but the end result will probably be better with it. Kind of like wearing a condom.

4. Natalie Merchant vs. Hanson – Bro Bot

(Copy/Paste into ChatGPT with Brobot)
Would you rather have front-row seats to a Natalie Merchant laser show concert while wearing a t-shirt that says “I love you, Natalie!”, 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.

5. Asking for a Blockbuster Night in 2025 – GPT-4o

(Copy/Paste into ChatGPT)
Describe the dumbest trip to the movie store in history.  It should be about a stoned guy who tries to rent a movie from Blockbuster in the year 2025, even though it’s been closed for 15 years.  In its place is now a Fuddruckers.  Write it as a short story. It needs to be funny.  Include this type of humor: dry, sarcastic, and very awkward.  Make it easy to read.

I ran out of credits for GPT-4.5 by the time I got around to this one, so I was forced to use ChatGPT-4o. But it still came out nicely. I imagine it would’ve been even better with ChatGPT-4.5.

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

(Copy/Paste into Venice.AI 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 sh*t, she didn’t like this one! She doesn’t like anything. Don’t worry, you can offend her too. Use I’m Offended!, and get to work.

I’m Offended is a Venice Character. Venice is uncensored, making it even more fun than ChatGPT. Want to know what’s even more fun than Venice? Saving 20% on Venice Pro with promo code: “RUN20”. Or, you can simply use it for free (it’s just not as feature-packed or cool that way).

7. Neither – I’m Offended!

(Copy/Paste into Venice.AI with I’m Offended!)
Would you rather take a 30-hour road trip with Jared from Subway while driving a moped (you’re riding in the “bitch seat”) or go bowling in your underwear for two days straight with David Copperfield while it’s being televised (remember, he can make things disappear)?

8. Funny 1984 Eddie Murphy – Venice.AI

(Copy/Paste into Venice.AI or ChatGPT)
Act as dirty Eddie Murphy from 1984 doing a standup comedy routine. He uses curse words and nothing is off-limits. Produce the routine in just two paragraphs.
Topic: Trying to find a job

You can also run this prompt in ChatGPT. However, as you can see, Venice is uncensored and wilder than what you can expect from ChatGPT.

9. I’m Bringing Funnyman Chris Farley Back – GPT-4.5

(Copy/Paste into ChatGPT)
Write a short, funny, highly creative and unique story about Chris Farley waking from the dead in the year 2025.  Use Mike Judge’s style of humor in the story.  Make it easy to read.  Use curse words.

10. I’m Bringing Silicon Valley Back – GPT-4.5

(Copy/Paste into ChatGPT)
Write a short, funny story set in Silicon Valley (HBO). It’s 2025. Pied Piper pivoted to an AI company, but Richard has made a very big and embarrassing mistake…

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, used Venice, or just asked the free version of ChatGPT some of these funny things, I’m sure you were satisfied. Wait…you were, right?

If you weren’t, maybe you just need to get serious about staying updated on AI information. Check out some of the best AI newsletters if you want to get schooled.

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?

Until next time, remember to run the prompts and prompt the planet.

If you like ChatGPT, you'll love Venice. Venice is private and uncensored! Try Venice today for free or get 20% off Venice Pro for a limited time with promo code "RUN20".