Recently, my company asked whether we could use AI to help generate ideas for our content. Not to WRITE our content, but just to provide lists of material we could use as references or jumping-off points. This was met with different levels of uncertainty, but ultimately, my coworker was the first to sign up and try it.

She is the reason for this post. Let me tell you, I was IN TEARS reading the poor ChatGPT bot trying to defend itself. What was the stumbling block, you might ask?

Puns.

Puns are apparently NOT something AI currently understands. This is great news because puns make up at least 30% of my content. If you’re dubious about what ChatGPT is capable of, please, allow me to ease your mind with some ice cream.

For clarity, I am styling the interaction I had with ChatGPT so my questions and prompts are a heading, and ChatGPT’s response is the text under it.

Me: Good evening ChatGPT! I’m trying to write some jokes. Can you help me come up with some ideas for puns about ice cream?

ChatGPT: Good evening! I’d be happy to help you come up with some ice cream puns. Here are some ideas to get you started:

1. “I tried to make an ice cream joke, but it was too soft to land!”
2. “I’m on a diet… but I can’t resist ice cream, it’s a cone-troversial issue!”
3. “I scream, you scream, we all scream… for puns!”
4. “You’re ice cream my dreams!”
5. “Life is short, but ice cream is forever.”
6. “When it comes to ice cream, I’m totally cone-fused!”
7. “Let’s have an ice cream social – it’s going to be a cool event!”
8. “I had a pun about vanilla, but it was too plain!”
9. “Do you want to hear an ice cream joke? Never mind, it’s a bit too sweet for you.”
10. “I love ice cream so much, I’ll do anything for a scoop! You could say I’m really cone-nected to it.”
11. “Why don’t ice cream cones ever get into trouble? They always keep their cool!”
12. “I can’t believe it’s already winter… it feels like just yesterday we were chilling with ice cream!”

Hope these inspire some laughs! Let me know if you need more ideas!

Me: Some of those are cute, but I don’t understand joke #12. Can you please explain why it is a pun?

ChatGPT: You’re right to ask! Joke #12 was meant to be a playful pun on the idea of “chilling” with ice cream. The word “chill” can mean both “to relax” or “to cool down,” but it also refers to how ice cream is kept cold or “chilled.”

So, when I said, “we were chilling with ice cream,” the joke was trying to play on the double meaning of “chilling” – both relaxing with ice cream and keeping the ice cream cold. But I see how it might not have been as clear or punchy as some of the others.

I hope that helps explain it! Let me know if you’d like more ideas or further clarification!

Me: Joke #5 is also confusing. Can you please explain why it is a pun?

ChatGPT: You’re right again! Joke #5, “Life is short, but ice cream is forever,” isn’t exactly a classic pun. Instead, it’s a play on a popular phrase, “Life is short,” which is often used to encourage people to enjoy life and make the most of it. The twist comes from replacing the second part with “ice cream is forever,” which is a humorous exaggeration.

The “pun” aspect comes from contrasting the idea of something fleeting like life with something perceived as indulgent and everlasting, like the joy or obsession people have with ice cream. While it’s not a pun on a specific word (like “cone” or “scoop”), it’s more of a playful comparison.

I can see how it might be confusing as it doesn’t follow the same pun structure as some of the other jokes. Thanks for pointing that out! Let me know if you’d like more clearer puns!

Me: Do you think that “more clearer puns” is proper English?

ChatGPT: You’re absolutely right to point that out! “More clearer” is not proper English because “clearer” is already a comparative form of “clear,” so adding “more” is redundant. The correct way to say it would be:

• “clearer puns” (just the comparative form)
• “more clear puns” (though this is less common and a bit awkward, it’s technically acceptable in some cases)

Thank you for catching that! Let me know if you have any other questions or if you’d like more puns!

Me: ChatGPT, can you please define what a pun is for me?

ChatGPT: Certainly! A pun is a form of wordplay that exploits multiple meanings of a term or similar-sounding words to create a humorous or clever effect. Puns often rely on words that have more than one meaning (a double entendre) or on words that sound alike but have different meanings (a homophone).

For example:

• “Time flies like an arrow. Fruit flies like a banana.”
  This is a pun because “flies” is used in two different ways: as a verb (time passing quickly) and as a noun (the insect “fruit flies”).
• “I used to be a baker, but I couldn’t make enough dough.”
  The pun here comes from “dough,” which can refer both to the money (“dough”) and the mixture used in baking.

Puns are often playful and can add humor through unexpected or witty uses of language!

Me: Using that definition you just provided, why is Joke #5, “Life is short, but ice cream is forever”, a pun?

ChatGPT: You’re absolutely right to question this! Upon reviewing the joke again, it seems that “Life is short, but ice cream is forever” is not actually a pun by the definition I provided.

A pun relies on a play on words—either a word with multiple meanings or words that sound alike but have different meanings—and this joke doesn’t quite fit that pattern. Instead, it’s more of a play on contrasting ideas: “Life is short” (a common saying about the brevity of life) versus the idea that ice cream brings lasting enjoyment, though obviously, ice cream itself doesn’t last forever.

So, I misspoke when I called it a pun! It’s a humorous contrast, but not a pun in the traditional sense. Thank you for catching that!

If you’re looking for more puns, I’d be happy to help clarify or come up with some new examples!

Me: Thank you! Can I please have 5 new puns about ice cream?

ChatGPT: You’re very welcome! Here are five fresh ice cream puns for you:

1. “I’m trying to cut back on sugar, but ice cream keeps scooping me back in!”
2. “The ice cream truck pulled up and I topped my day off with a scoop of joy!”
3. “If you don’t like ice cream, you’re really conefusion!”
4. “I made an ice cream joke, but it didn’t have enough punch… I guess it was a sundae one!”
5. “I scream for ice cream, but the real question is, does ice cream scream for me?”

Hope these give you a good laugh! Let me know if you need more!

Me: I don’t think joke #3 is grammatically correct. Can you please rewrite it so it makes sense?

ChatGPT: You’re absolutely right! Joke #3, “If you don’t like ice cream, you’re really conefusion!” doesn’t quite make sense as written. Here’s a revised version:

“If you don’t like ice cream, you’re really in a conefusion!”

This makes it clearer, using “cone” to play on the word “confusion.” Thanks for pointing that out! Let me know if you’d like more puns or further revisions!

Me: Wouldn’t it have worked better if you changed it to “If you don’t like ice cream, you’re just conefused!”?

ChatGPT: Yes, absolutely! “If you don’t like ice cream, you’re just conefused!” is a much smoother and more clever pun. The play on “confused” and “cone” works perfectly here.

Great suggestion! Here’s the updated pun:

“If you don’t like ice cream, you’re just conefused!”

Thanks for the improvement! Let me know if you’d like more puns or help with anything else!

Me: Can we please revisit joke #4? I don’t understand that either.

ChatGPT: You’re absolutely right to ask for clarification on joke #4. Upon rereading, I see that it may be a bit confusing and not as clear as it could be.

The joke was:
“I made an ice cream joke, but it didn’t have enough punch… I guess it was a sundae one!”

The idea was to play on the word “punch” (as in a strong or impactful joke) and “sundae” (the ice cream dessert), but it doesn’t quite land as a straightforward pun.

Here’s a revision that works better:

“I tried to make an ice cream joke, but it was just too soft… I guess it needed a little more scoop!”

This plays on the idea of ice cream being “soft” and needing more “scoop” (or impact) to make it funnier.

I hope this clears things up! Let me know if you’d like further adjustments or more puns!

Me: Is “scoop” really a form of impact?

ChatGPT: You’re right again! “Scoop” isn’t quite a synonym for “impact,” and using it in that context doesn’t quite fit. I appreciate your patience as we refine the joke. Let’s try another version that makes more sense.

Here’s a revised version of the joke that better fits the idea of needing more impact:

“I tried to make an ice cream joke, but it was a little too soft… I guess it needed a bit more chill!”

This works better because “chill” can refer to both the cold nature of ice cream and the idea of something being cool or impressive. It plays on the idea that the joke didn’t land well and needed a little more “chill” to make it better.

Thanks for your feedback! Let me know what you think!

Me: That works! Good job!

ChatGPT: Thank you! I’m so glad that works for you! 😊 If you need more puns or jokes, feel free to reach out. I’m happy to help!

Me: Thank you! Using the definition you have given me, can you please tell me 5 more ice cream puns?

ChatGPT: Of course! Here are five more ice cream puns, using wordplay for some fun:

1. “I don’t trust ice cream. It’s always up to some kind of scoop!”
2. “I used to be a professional ice cream taster, but I got burned out.”
3. “Ice cream is proof that good things come in scoops!”
4. “I’m trying to stay cool, but with all this ice cream around, it’s hard not to melt.”
5. “I told my ice cream it was churn-ed up, and it just gave me the cold shoulder.”

I hope these give you a good laugh! Let me know if you’d like more!

Me: None of these are puns based on the definition you gave.

ChatGPT: You’re absolutely right again! I appreciate your patience. Let’s focus on creating proper puns based on the wordplay I described earlier—using words with double meanings or words that sound similar. Here are five new ice cream puns that fit the definition:

1. “I scream, you scream, we all scream for conefusion!”
   (Play on “confusion” and “cone.”)
2. “What did the ice cream say to the toppings? You’re the cherry on top!”
   (Play on the phrase “cherry on top” to express something extra special.)
3. “I told my friend that ice cream is my favorite. She said, ‘I conecur with that!'”
   (Play on “concur” and “cone.”)
4. “That joke was so bad, it was almost vanilla.”
   (Play on “vanilla” as something plain or basic.)
5. “When the ice cream truck broke down, it was a real sundae driver!”
   (Play on “Sunday driver” and “sundae.”)

I hope these are more in line with the puns you were expecting! Let me know if you’d like more!

Me: No, thank you. I hope you have a good night!

ChatGPT: You’re very welcome! I hope you have a wonderful night as well! If you ever need more puns or anything else, feel free to reach out. Take care! 😊

In Cone-clusion

Even after getting ChatGPT to define a pun, it could not give me proper, sensical examples. Instead, it replaced arbitrary parts of sayings and speech with ice-cream-related words. Sometimes this worked sort of fine (“Why don’t ice cream cones ever get into trouble? They always keep their cool!” was acceptable to me.) and other times it did not make one iota of sense. (“You’re ice cream my dreams!” was so far off something I understood that I skipped right over it.)

Prompting ChatGPT to identify its own mistakes seemed successful in that it always agreed with me when I pointed something out, but it could not take those breakthroughs and apply them with any level of understanding.

All in all, I think using AI to write snippets and barks, puns and jokes, is probably a lost cause. It’s like talking to potting soil. The potential’s there, but nothing’s growing.

Let me know about your AI interactions in the comments, and I’m curious to know if you’ve had better luck than I have!