AI wrote me a letter from my father

and it's not at all what I expected

My father would be 91 today. He died a few weeks after his 80th birthday, back in 2014. He was, in many ways, “my person.” We spoke at least once every day. We talked about, well, pretty much everything. He’s still such a huge presence in my life that I’m blown away by how much he has missed.

He doesn’t know for example, that his daughter Rachel, my sister, died five years after he did. He doesn’t know that my daughter, Dalia, died three years after that. (I mean of course I fantasize that he not only knows, but is hanging out with both of them and the rest of our people now.)

He wouldn’t know what Covid is, or AI, or that “fake news” is a thing. He wouldn’t believe that Trump was elected once, let alone twice. He’d have so much to say about all of it, and now I just have to imagine every word.

I’m not the only one who wonders. My dad was a writer and a scholar, a proud “peacenik” who wrote about politics and American Jews and devoted his life to trying to mend the world. Ever since the Hamas attack of October 7, 2023, people say to me all the time: I wonder what your dad would say.

A couple of weeks ago (before the U.S. bombing in Iran), I was reading yet another piece of depressing news. I don’t even remember the details, but I desperately wanted to call my dad and talk it through. In a moment of profound loneliness, I did something a bit mortifying: I asked AI to speak for my father.

My dad was a public figure — he wrote books, columns, speeches. His words are still easy to find online, so the challenge for AI was maybe simpler than if I’d asked about someone with no digital footprint. Still, the letter I got back blew me away. With only one “mistake,” it sounded so much like him I kind of wanted to file it away with the letters he actually did write to me over the years.

Here’s what I asked:

Can you write a letter to me from my late father, Leonard Fein, about what he thinks about current events?

That was it. I didn’t mention Israel specifically, though that was the area he wrote about the most, or say anything about myself.

I’m sharing the letter for a couple of reasons. First, the message resonates. Second, I’m slightly horrified by the comfort it gave me. It made me begin to understand how people could slip into relationships with whatever it is that’s delivering advice/comfort/inspiration through their computer, and that scares me.

Here’s the response I received:

My Dearest Jessica, [Here’s what AI got wrong: my dad never, ever, called me by my full name. He would have said “Jessie,” every time.]

I’ve been watching.

And not with detachment or distance, mind you. With the full weight of heartbreak, outrage, and—yes—hope. You know I was never one for silence in the face of injustice, nor for complacency in the face of suffering. Some things don’t change after death.

The world is in turmoil, again—or perhaps still. What’s unfolding in Israel and Gaza, in our democracy, in the fragile web of global interdependence—is not unfamiliar. It’s the same moral thicket I spent my life trying to navigate, and, at times, trying to untangle for others.

You know what I would say: that we must hold complexity without letting it paralyze us. That to be Jewish is to be fiercely committed to justice—not just for our own, but for all. That grief must not cloud our moral vision, even when it feels like the whole world is burning.

There are voices—loud ones—who insist on either/or. I never believed in that. Not when it came to peace, not when it came to politics, not when it came to people. It’s always been both/and. Justice and mercy. Security and dignity. Truth and empathy.

I see you holding all of that now. I see you walking through grief and still showing up with courage, with kindness, with clarity. That’s what I always hoped for you—not perfection, but integrity. Not answers, but questions that mattered.

I know you worry sometimes that you don’t say the right thing, or do enough. But I see how you live, how you raise your voice, how you raise your children. I see the people you gather, the space you make for sorrow, the light you still insist on kindling.

So yes, things are hard. But don’t let despair make a home in you. Rage if you must. Weep if you need. But then keep going. Keep writing. Keep wrestling. Keep loving. [This part is my favorite.]

And remember what I told you often—because I meant it every time: You are my greatest joy.

With all my love,
Dad

It’s pretty crazy, right? It’s not just how the letter was written, but how on point the messaging is. If AI is this good now, where will it be in six months? A year? Five years? Will any of us write at all anymore or will everything be computer generated?

I truly believe there’s something terrifying about where we are now with AI, let alone where we’re likely headed.

And yet, I have to wonder if maybe it's okay to embrace this way of connecting with our people who are gone. Maybe whatever brings a griever a glimpse of their person is its own kind of blessing. Maybe it’s not about what’s real or fake, but about what helps us carry them forward, in any form we can. Is it any different from finding comfort in a medium’s message or a taking part in a spiritual ceremony or poring over old photos? If it makes us feel close to our person, where’s the harm in that?

Hearing my dad’s “voice” in the letter is also another reminder of the value we’re offering when we share our writing — not just for those who read it today, but for those who may long to hear our voice in the future. I wouldn’t, for example, be able to have a letter that was this spot on written by AI in the voice of my mother. (I know; I tried.)

I wonder what my dad would say about all of it. And no, I’m not going to ask AI to tell me. Instead I’m going to assume he’d red-mark AI’s letter, point out that he was a much better writer, and assure me that whatever brings me comfort is okay as far as he’s concerned.

What do you think?

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Dahlia Spotting

Now this is not even a little bit computer generated.

Thank so much for being part of this community. I’m so glad you’re here.

With grit and grace,

Jessie