ChatGPT mocks Don Rickles. I’m worried about AI.

AI For Business


Have you ever heard about the time Don Rickles tried to talk to Lena Dunham in the middle of the night?

no? Let me explain. First, we have to talk about Reese Witherspoon.

You see, I’m a simple woman. I only have two interests. Technology news and celebrity gossip. So I was naturally intrigued by the recent online uproar over Reese Witherspoon’s recommendation that women learn how to use AI. This caused so much backlash that she had to issue an additional explanation.

I was also intrigued by Lena Dunham’s new book. (They are kind of related. Keep reading!)

I think Reese is mostly right about AI. She says the same thing other business leaders are saying. But her comment made me think a little more. ”Learn how to use AI“Writing emails in ChatGPT? Understanding the technology behind different models? Vibe coding? What level of ‘AI usage’ is expected here to keep up in the workforce and life in general?


Reese Witherspoon getting out of a Cadillac Escalade

Reese Witherspoon really wants us to learn how to use AI

Media Punch/Bauer Griffin/GC Images



One of my areas of focus is using ChatGPT as a kind of super Google. know Although it’s online, it takes some effort to dig it up with regular search engines.

Is this a recent example? It is, of course, related to celebrity gossip.

I was reading Dunham’s new memoir, Famesick, and it was full of moderately provocative celebrity gossip and blind items about the people named. Celebrity gossip is a fun little riddle for readers to solve, giving some clues about a person’s identity without naming them.

One of the blind items concerns an anonymous male celebrity who — after meeting Lena backstage during the filming of “The View” in 2012 — allegedly sent her a flirtatious text message in the middle of the night. I thought I could solve this blind item by finding out who the other guests on the same episode were. I’m sure that information is online somewhere, but it takes forever to find it.

So I asked ChatGPT to identify the male guest on that year’s episode of “The View,” which Lena also appeared on. At first, ChatGPT told me there were only four female cast members on the show. When asked again who the other male guest would be, Chris Evans and Chris Hemsworth were suggested. (Not really. According to IMDb, they appeared in separate episodes in the same year.)

That time Don Rickles talked to Lena Dunham

As Dunham described this guy, when I said, “No, he’s a comedian,” ChatGPT confidently gave a new answer. It was legendary comedian Don Rickles who texted Dunham after the show.

I laughed out loud as I thought of all the possibilities of who could have sent me a “Are you awake?” message in the middle of the night. I think the text is true do not have Don Rickles was 85 years old at the time.

Dunham said of the man, “A bit like the American Hugh Grant, he was famous for his loquacious charm and ability to charm his on-screen lovers with his fast-talking, hand-flapping anxiety. Ostensibly a comedian, he was there to promote a gothic film with dramatic twists.” It doesn’t sound like a Don Rickles Borscht Belt insult cartoon to me.


Don Rickles

An undated historical photo of legendary insult comedian Don Rickles. Did he text Lena Dunham late at night? ChatGPT says so.

Ron Galella/Ron Galella Collection (Getty Images)



After spending so much time looking for an answer to this on the internet, and searching the old-fashioned way, I can now make some guesses as to how and why ChatGPT was so wrong here. IMDb’s episode guides for 2012 episodes of “The View” are spotty, with some episode entries missing information about the guests and no video clips accessible online. The only evidence I found that Lena Dunham ever appeared on “The View” on April 20, 2012, was a Vulture blog post from that day that had an embedded YouTube clip marked as private.

Knowing this, you can see how the AI ​​got confused. When information is missing, AI sometimes becomes vague about what it understands. can I’m trying to come up with a plausible answer. Chris Evans and Chris Hemsworth appeared on the May 4, 2012 episode of “The View,” and Dunham and Rickles appeared together on a 2016 episode.

The fact that ChatGPT does something like this (basically guessing what you want to hear) might be useful if you’re trying to write an email to a friend. Obviously it doesn’t help if you’re looking for specific facts and are just making something up.

For the record, neither Lena, Don (who passed away in 2017), nor the National Comedy Center, the custodian of the Rickles Archive, responded to my requests for comment.

Are we stuck in the pizza glue loop?

Look, I understand. Pointing out what ChatGPT is doing wrong in the spring of 2026 isn’t particularly interesting. We, at least all of us, know this. should Please know this. Still, I keep encountering many things clear Mistakes when asking AI for facts. These are the obvious mistakes I found. know What is generated by AI? do not have correct answer.

But what about the mistakes I don’t notice or don’t even notice? What I blindly accept as fact? You’re always double-checking work-related things, but are you actually saving time?

How quickly will this improve? Are we stuck in the pizza glue loop forever? teeth this What on earth is causing so many lawyers and tax CPAs to lose their jobs? I mean, okay, sure.

This is where the ideas of Witherspoon and other bosses come into play.Learn how to use AI!“It’s frustrating. I’m pretty confident in using different AI tools and have a good concept of how they work. I’m a woman and I learned how to use AI! And yet here I am and I’m still not satisfied.

There’s a gap between what Reese Witherspoon wants from me, what I want from AI, and the wholesome image of comedy legend Don Rickles. So far, those things haven’t worked out.