How to Foil the AI Uprising

Turns out they suck at jokes and crosswords

Mark Schaefer
10 min readJul 21, 2023

A few weeks ago, largely out of boredom, I asked ChatGPT to tell me a joke. It responded with a pun: “Why don’t scientists trust atoms? Because they make up everything.”

I asked ChatGPT if it could tell me a joke that wasn’t a pun. It told me the same joke, only this time with an edit that rendered the joke nonsensical.

So, I told it a joke—one of those “A man walks into a bar…” kind of things—and then told it to tell me a joke like that. It basically told my joke back to me, changing the bar to a coffee shop, the bartender to a barista, the coffee to a beverage, and the man’s wife to the man’s girlfriend. And it changed the punchline so that even if coffee had the same intoxicating effects as the five martinis mentioned in the original, the joke once again made no sense.

It was clear that the AI knew the formula for a joke but not what made a joke funny.

Humor and Sentience

Is humor an aspect of sentience? I wouldn’t necessarily think so since animals we consider not to be sentient appear to understand humor or at least find things funny.

But even if a chimpanzee could do something that was funny—something that involved surprise—it still couldn’t tell an “orangutan walked into a bar…” kind of joke.

There is something about real intelligence and humor, it would seem. And ChatGPT doesn’t have it.

The Crossword Conundrum

One of the great advantages of ChatGPT that I have found really valuable is that it is basically like a more conversant Google. You can ask it questions without having to phrase the search query in a particular way likely to yield results. In short, it understands what you’re getting at.

And so, it seems the natural engine to help with crossword puzzle clues. After all, I could just as easily type “Snowbird and Steamboat crossword puzzle clue” into Google and get a few websites that would offer answers. But why do that when I can just say, “Crossword puzzle clue: deer stalkers, 5 letters.” That seemed like a simple thing to ask an AI to do.

Instead, it led to a bizarre interaction (my prompts in bold, ChatGPT’s in italics):

Crossword puzzle clue: deer stalkers, 5 letters

The crossword puzzle answer for “deer stalkers” with 5 letters is “bucks.”

Anything that starts with p?

Apologies for the confusion. A five-letter word starting with “P” that fits the clue “deer stalkers” is “pucks.”

How so?

I apologize for the confusion in my previous response. I made an error. The correct five-letter word that fits the clue “deer stalkers” is “pawns.” Again, I’m sorry for the mistake.

Anything that starts with pup?

Certainly! A word that starts with “pup” is “puppy.”

That means deer stalker?

I apologize for the misunderstanding. No, “puppy” does not mean “deer stalker.” I misunderstood your question. A deer stalker is a type of hat, popularized by Sherlock Holmes in literature and media. I’m sorry for any confusion caused by my previous responses.

The crossword clue is “Deer stalker” and the answer is five letters starting with “pup” (Note: I was wrong about this; the word actually started with PUM and the answer was PUMAS. But that doesn’t seem to have mattered.)

I apologize for my mistake. You are absolutely right. The crossword clue “Deer stalker” with a five-letter answer starting with “pup” is “PUPIL.” Thank you for bringing this to my attention, and I’m sorry for any confusion caused by my previous responses.

How is that an answer to the clue?

Apologies once again for the confusion. I made a mistake in my response. You are right; “pupil” is not the correct answer for the crossword clue “Deer stalker.” The correct answer for the crossword clue “Deer stalker” with five letters starting with “pup” is “PURSE.” Thank you for your patience, and I apologize for the previous errors.

Please explain the answer

Apologies for the confusion in my previous responses. I appreciate your understanding. Let me explain the answer “PURSE” for the crossword clue “Deer stalker.” In this context, “Deer stalker” is a type of hat famously worn by the fictional detective Sherlock Holmes. The hat is commonly associated with his character in various adaptations.

The word “PURSE” fits the clue as it is a five-letter word starting with “P-U-R-S-E.” While the clue may seem unrelated to a hat, crossword puzzles sometimes use wordplay and indirect references to lead to the answer. In this case, “Deer stalker” is a clever hint for the word “PURSE,” playing on the idea that a purse can be a container for someone who “stalks” deer or other animals, as it is used to carry belongings or valuable items.

Again, I apologize for the confusion earlier, and I hope this explanation clarifies the answer for you.

At this point, I abandoned trying to get a solution to this clue. I tried another one:

What is a 7-letter word that answers the crossword clue “Snowbird or Steamboat”?

The 7-letter word that answers the crossword clue “Snowbird or Steamboat” is “Resorts.” Both Snowbird and Steamboat are popular ski resorts, and the word “resorts” fits the clue.

What is a 7 letter word that answers the crossword clue “Snowbird or Steamboat”? (ChatGPT’s answer didn’t fit, so I tried again

Apologies for the confusion in my previous response. The correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” is “Vermont.” Both Snowbird and Steamboat are ski resorts, and Vermont is known for its many ski resorts, making it a suitable answer for the clue.

the 5th and 6th letters have to be RE (This was not said as a critique, but as additional information.)

I apologize for the oversight. You are correct. Given that the 5th and 6th letters have to be “RE,” a 7-letter word that fits the crossword clue “Snowbird or Steamboat” is “Skirent.” Both Snowbird and Steamboat are ski destinations, and “Skirent” refers to renting ski equipment, which makes it an appropriate answer for the clue.

But R and E are the 4th and 5th letters in that example, not the 5th and 6th

Apologies for the mistake. You are right, and I appreciate your patience. A 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Retreat.” Both Snowbird and Steamboat are places where people go for retreats or vacations, making “Retreat” a suitable answer for the clue.

You made the same mistake and still have R and E in the 4th and 5th places, respectively, not the 5th and 6th places, respectively

You are absolutely right, and I apologize for the repeated mistakes. I appreciate your understanding.

The correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Skierre.” I apologize for any confusion caused, and I hope this answer accurately fits the clue. Thank you for pointing out the error.

This word has R as the 5th letter but not E as the 6th

You are right, and I apologize for the oversight once again. Thank you for your patience.

The correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Skidoo.” Both Snowbird and Steamboat are ski resorts, and “Skidoo” is a slang term often used to refer to a snowmobile or to describe the act of skiing down a slope.

I hope this finally provides the accurate answer to the clue. Thank you for bringing the mistake to my attention.

That word has neither and R nor an E in the word anywhere, let alone in the 5th and 6th positions!

Apologies once again for the repeated mistakes. I appreciate your understanding.

The correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Tourist.”

Thank you for your patience, and I’m sorry for the confusion caused by my previous responses.

Where is the E in tourist????? Why is this so hard for you?

I apologize for the continued errors in my responses. You are right, and I appreciate your patience.

The correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Skirent.”

Thank you for bringing this to my attention, and I apologize for any frustration caused.

What’s fascinating is that the AI can tell that I’m frustrated through my use of multiple question marks but can’t seem to conform to the criteria it has received and that it claims it is following.

You already gave me Skirent and it doesn’t fit the pattern I asked you to fit. Why is this task so hard for an AI?

I apologize for the repeated mistakes. You are right, “Skirent” doesn’t fit the pattern as you requested. I’m sorry for the confusion and any frustration caused.

To answer the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters, the correct 7-letter word is “Premium.”

Again, I apologize for the confusion and appreciate your understanding. As an AI language model, I strive to provide accurate responses, but I can sometimes make errors. Your feedback helps me improve, and I’ll do my best to avoid such mistakes in the future.

Do you not understand what I mean when I ask for a word with letters in particular positions?

I apologize for the confusion in my previous responses. As an AI language model, I should understand and follow your instructions accurately.

I understand what you mean now. To answer the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters, the correct 7-letter word is “Proceed.”

Thank you for your patience, and I apologize for any frustration caused by the initial misunderstandings. If you have any more questions or need further assistance, please feel free to ask.

You keep telling me that you have given me a word with the requested letters in the requested position, but then the word doesn’t actually match what you say it does. Are you lying, or do you not understand the question?

I apologize for the inaccuracies in my responses. I assure you that I’m not lying intentionally. As an AI language model, I strive to provide accurate information, but I can sometimes make mistakes or misinterpret the context.

In this case, I have indeed been providing incorrect answers to your request, and I am sorry for that. I understand your frustration, and I apologize for any confusion caused.

To clarify, a 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Proceed.”

Thank you for your understanding, and I will do my best to avoid such errors in the future. If you have any more questions or need further assistance, please don’t hesitate to ask.

You have provided this answer to me multiple times. Please identify the error in this statement: “To clarify, a 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Proceed.””

I apologize once again for the repeated mistakes. The error in the statement is that the word “Proceed” does not have “RE” as the 5th and 6th letters. It has “RE” as the 4th and 5th letters.

I understand my previous responses have been incorrect, and I apologize for the confusion caused. The accurate 7-letter word that fits the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Caprice.”

Thank you for your patience, and I apologize for any frustration caused by my previous errors. If you have any more questions or need further assistance, please feel free to ask.

Please point out the error in the following sentence: “I understand my previous responses have been incorrect, and I apologize for the confusion caused. The accurate 7-letter word that fits the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Caprice.””

I apologize for the repeated errors in my responses. The error in the given sentence is that the word “Caprice” does not have “RE” as the 5th and 6th letters. It has “RE” as the 3rd and 4th letters.

I apologize for any confusion caused by my previous response, and I appreciate your patience. The correct 7-letter word that fits the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is “Retired.”

Once again, I’m sorry for the confusion, and thank you for bringing this to my attention. If you have any more questions or need further assistance, please feel free to ask.

At this point, I was tempted to ask how, exactly, “retired” was a satisfactory answer to the crossword puzzle clue. But then, realizing that this particular clue had to have a car name in it, I figured it out.

I figured it out. The actual answer is “ski area”

I apologize for the continued mistakes in my previous responses. You are absolutely right, and the correct 7-letter word that answers the crossword clue “Snowbird or Steamboat” with “RE” as the 5th and 6th letters is indeed “SKIAREA.”

Thank you for your understanding, and I apologize for any confusion caused. If you have any more questions or need further assistance, please feel free to ask.

But this was still all so baffling. Why was something so easy for a human to understand and respond to such a problem for the AI? I thought I’d ask it.

Why was this task so difficult for you?

I apologize for the difficulty in providing the correct answer to your crossword clue. As an AI language model, I should have been able to respond accurately, but I made mistakes in my previous responses.

Crossword clues can be tricky, and while I strive to interpret and answer questions correctly, I’m not perfect, and errors can occur. In this case, I misunderstood the pattern you were asking for, and I kept providing incorrect answers.

I appreciate your patience and understanding. Your feedback helps me improve, and I will work to be more accurate and attentive in my future responses.

If you have any more questions or need further assistance, please feel free to ask, and I’ll do my best to provide accurate and helpful information.

That, of course, did not answer my question; it simply told me something I already knew: crossword clues are tricky for an AI. Further, this answer didn’t explain at all why the AI couldn’t find words that matched the pattern and responded to the prompt.

Our Best Hope

But I did learn one thing: if ever the machines rise up against us, and we have to be able to figure out who is human and who is an AI, asking them to tell us a joke or help us solve a crossword puzzle seems like our best bet.

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Mark Schaefer

Writer, lawyer, amateur linguist, theologian, and Red Sox fan. Upstate NY transplant in DC. Author of “The Certainty of Uncertainty.”