Lena Dunham Left a Clue, so AI Told Me: It Was Don Rickles Who Texted.

Did you hear about the time Don Rickles tried to chat up Lena Dunham in the middle of the night?

No? Let me explain. First, we need to talk about Reese Witherspoon.

See, I’m a simple woman. I have only two interests: tech news and celebrity gossip. So I was naturally intrigued by a recent online fuss over Reese Witherspoon’s admonition for women to learn to use AI. It sparked so much backlash that she had to issue a follow-up explanation.

I’ve also been intrigued by Lena Dunham’s new book. (They’re related — sort of. Keep reading!)

I think Reese is generally right about AI — she’s saying the same thing that every other business leader is saying. But her comments did make me think a little more about what “Learn to use AI” even means. Writing emails with ChatGPT? Understanding the technology behind different models? Vibe coding? What level of “using AI” is expected here to stave off falling behind in the workforce and life in general?

One area I’ve really leaned into is using ChatGPT as a sort of super Google — to find something I know is online but would take some effort to dig up with a normal search engine.

A recent example? It’s related to — of course — celebrity gossip.

I was reading Dunham’s new memoir, “Famesick,” which is full of moderately juicy celebrity gossip about named people and also blind items — celebrity gossip that gives a few clues about the identity of the person without naming them, a fun little riddle for the readers to solve.

One blind item is about an unnamed male celebrity who — allegedly — sent Lena a flirty late-night text message after meeting her backstage while taping “The View” in 2012. I figured I could solve this blind item by finding out who the other guest was on the same episode — information that should be online somewhere, but would take me forever to find.

So I asked ChatGPT to identify the male guest on “The View” episode that Lena was also on that year. At first, ChatGPT told me that it was only the four female cast members from the show. When I asked again who the other male guest was, the suggestions were Chris Evans and Chris Hemsworth. (Not so. They appeared on a separate episode that same year, according to IMDb.)

That time Don Rickles chatted up Lena Dunham

When I said, “No, a comedian,” as Dunham had described the man, ChatGPT confidently provided a new answer: It was legendary comedian Don Rickles who’d texted Dunham after the show.

I laughed out loud because of all the possibilities of who sent a late-night “u up?” text, I feel fairly certain it was not Don Rickles, who would’ve been 85 years old at the time.

Dunham’s description of the man: “a bit of an American Hugh Grant, famous for that sort of chattery charm and his ability to woo his onscreen paramours with his fast-talking, hand-flapping anxiety. Ostensibly a comedian, he was there to promote his Gothic-tinted movie, where he had made a dramatic turn.” Doesn’t exactly sound like a Borscht Belt insult comic Don Rickles to me.

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

Knowing this, I can start to see how AI got confused: When there’s a lack of information, AI sometimes blurs together what it can find to try to spit out 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 an episode in 2016.

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

For the record: Neither Lena nor Don (who died in 2017) nor the National Comedy Center, which is the keeper of the Rickles archive, responded to my requests for comment.

Are we stuck in a pizza glue loop?

Look, I get it. It’s not particularly exciting to point out that ChatGPT gets things wrong in the spring of 2026. We know this, or at least we all should know this. Still, I keep coming across so many obvious mistakes when asking AI for factual things. These are the glaring mistakes I catch when I know that what AI has generated is not the right answer.

But what about the mistakes that I don’t catch — or don’t even know to catch? Things that I blindly accept as fact? For work-related stuff, I’ll always double-check, but in those cases, am I actually saving myself any time?

How soon will this improve? Will we be stuck in a pizza glue loop forever? Is this what’s going to make a bunch of lawyers and tax CPAs lose their jobs? I mean, OK, sure.

Here’s where Witherspoon’s and other bosses’ idea of “Learn to use AI!” feels frustrating. I feel fairly confident about using various AI tools and have a decent concept of how they work. I am a woman, and I have learned to use AI! And yet, here I am, still unsatisfied.

There’s a gap between what Reese Witherspoon wants for me and what I want out of AI — and the wholesome image of comedy legend Don Rickles. For now, those things just aren’t lining up right.