ChatGPT and the Memory of Don Rickles: When AI Distorts Reality

ChatGPT and the Memory of Don Rickles: When AI Distorts Reality

Recently, I asked ChatGPT to identify an unnamed male celebrity who allegedly sent suggestive messages to Lena Dunham in 2012. To my surprise, the AI named Don Rickles, a claim that seems highly dubious to me.

This raises an important question: how should we approach the learning and use of artificial intelligence?

An Unlikely Anecdote

Have you ever heard about the incident where Don Rickles supposedly tried to flirt with Lena Dunham in the middle of the night? No? Let me explain. But first, let’s talk about Reese Witherspoon.

I am a person with simple interests: new technologies and celebrity gossip. That’s why I was intrigued by the recent online controversy surrounding Reese Witherspoon's call for women to learn how to use AI. This statement sparked so much reaction that she had to publish a follow-up explanation.

AI and Celebrity Gossip

My interest was also piqued by Lena Dunham's new book. These two topics are linked, in a way. Keep reading! Reese is generally right about the importance of AI, similar to the comments made by many business leaders. However, her remarks prompted me to think more deeply about what it really means to "learn how to use AI." Is it simply about writing emails with ChatGPT? Understanding the technology behind different models? Or mastering coding? What level of AI proficiency is necessary to avoid being left behind in the professional world and in daily life?

One way I explored this was by using ChatGPT as a sort of super search engine, to uncover information that I know is available online but would require considerable effort to find through traditional means.

An Investigation into Gossip

A recent example concerns, of course, celebrity gossip. While reading Dunham's new memoir, "Famesick," I discovered juicy anecdotes about celebrities, some named, others anonymous. An anonymous article mentioned a male celebrity who allegedly sent a flirty message to Lena after meeting her backstage during the taping of "The View" in 2012. I thought I could solve this mystery by discovering who the other male guest on that episode was, information that should be online but is difficult to track down.

I asked ChatGPT to identify that male guest from "The View" when Lena was present that year. Initially, ChatGPT claimed that there were only the four female members of the show. When I pressed further, the AI suggested Chris Evans and Chris Hemsworth, which was incorrect, as they appeared in a different episode that same year, according to IMDb.

An Unexpected Response

When I specified "a comedian," as Dunham had described the man, ChatGPT confidently responded that it was the legendary comedian Don Rickles who had sent a message to Dunham after the show.

I burst out laughing, because among all the possibilities of who could have sent a "are you awake?" message late at night, I am almost certain it was not Don Rickles, who would have been 85 at the time.

A Description That Doesn’t Fit

Dunham's description of the man: "a bit of an American Hugh Grant, famous for his chatty charm and ability to seduce his on-screen partners with his fast-talking anxiety and hand gestures. Apparently a comedian, he was there to promote his gothic-tinged film, where he had made a dramatic turn." This does not resemble a Borscht Belt insult comic like Don Rickles at all.

After spending a lot of time searching for answers online in a traditional way, I can make some guesses about how and why ChatGPT got it wrong here. The IMDb episode guide for "The View" in 2012 is uneven, with entries for some episodes lacking information about the guests, and no videos accessible online. The only evidence I found that Lena Dunham was ever on "The View" on April 20, 2012, was a blog post from Vulture that day, with an embedded YouTube clip marked as private.

The Limits of AI

Knowing this, I can start to see how the AI got confused: when there is a lack of information, AI sometimes mixes what it can find to try to provide a plausible answer. Chris Evans and Chris Hemsworth appeared in the May 4, 2012 episode of "The View," and Dunham and Rickles appeared together in an episode in 2016.

ChatGPT doing this kind of thing — essentially making a guess about what you might want to hear — could be useful if you’re trying to write an email to a friend, perhaps? It’s not helpful, obviously, if you’re looking for a specific fact and it just makes something up.

For the record: neither Lena nor Don (who passed away in 2017) nor the National Comedy Center, which holds Rickles' archive, responded to my requests for comment.

Are We Stuck in a Pizza Glue Loop?

Listen, I get it. It’s not particularly exciting to point out that ChatGPT gets things wrong in the spring of 2026. We know it, or at least we should all know it. Yet, I continue to encounter so many obvious errors when I ask the AI factual questions. These are the glaring mistakes I spot when I know that what the AI generated is not the correct answer.

But what about the errors I don’t spot — or don’t even know to spot? Things I blindly accept as facts? For work-related matters, I will always double-check, but in those cases, am I really saving myself time?

The Future of AI

How quickly will this improve? Will we be stuck in a pizza glue loop forever? Is this going to cost a bunch of lawyers and tax accountants their jobs? I mean, sure, okay.

This is where the idea from Witherspoon and other leaders of "Learn to use AI!" seems frustrating. I feel quite confident in using various AI tools and have a decent understanding of how they work. I’m a woman, and I’ve learned to use AI! And yet, here I am, still unsatisfied.

There is a gap between what Reese Witherspoon wants for me and what I want from AI — and the benevolent image of comedy legend Don Rickles. For now, these things simply do not align properly.