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Dylan Freedman

@dylanfreedman.nytimes.com

11K followers 330 following 410 posts

A.I. @nytimes.com My work: https://www.nytimes.com/by/dylan-freedman Contact: [email protected], dylanfreedman.39 (Signal) 🏃🏻 🎹

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Dylan Freedman @dylanfreedman.nytimes.com · Nov 11

Hello, new followers! I work at the intersection of A.I. and journalism. I think a lot about how to responsibly apply A.I. to investigate and hold the powerful to account — as well as build cool tools.

A recent piece I worked on that used A.I. + other data analysis: www.nytimes.com/2024/10/06/u...

Trump’s Speeches, Increasingly Angry and Rambling, Reignite the Question of Age

With the passage of time, the 78-year-old former president’s speeches have grown darker, harsher, longer, angrier, less focused, more profane and increasingly fixated on the past, according to a revie...

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Kashmir Hill @kashhill.bsky.social · 16d

A month after my last skeet, the subreddit "My Boyfriend is AI" now has 88,000 members and is the subject of an MIT study that found that "AI companionship emerges unintentionally through functional use rather than deliberate seeking."

arxiv.org/html/2509.11...

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Hannes Cools @hannescools.bsky.social · 22d

"Trapped in a ChatGPT Spiral." 🌀

Important work by @kashhill.bsky.social & @dylanfreedman.nytimes.com on how chatbots have a tendency to endorse conspiratorial and mystical belief systems. This shows again how conformist LLMs can be. Worth a listen 👇
www.nytimes.com/2025/09/16/p...

Trapped in a ChatGPT Spiral

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Dylan Freedman @dylanfreedman.nytimes.com · Sep 6

📸 Union Station, Washington, D.C.

Two men in military uniforms with rifles standing next to a sign that says “Welcome to Washington DC” and “Metro”

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Dylan Freedman @dylanfreedman.nytimes.com · Sep 6

The most wild thing to me about this story is how big $1.5 billion is: “$3,000 per work to 500,000 authors.”

Anthropic Agrees to Pay $1.5 Billion to Settle Lawsuit With Book Authors

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Stuart A. Thompson @stuartathompson.bsky.social · Sep 2

My colleagues and I tested different versions of Grok released since May to pinpoint how Musk has pushed the chatbot to the right www.nytimes.com/2025/09/02/t...

How Elon Musk Is Remaking Grok in His Image

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Kevin Schaul @kevinschaul.bsky.social · Sep 2

Great analysis of how Grok's political bias has changed. NYT tested Grok on a political bias survey, using different versions of its system prompt. Shows much tweaking these system prompts affects model outputs. https://www.nytimes.com/2025/09/02/technology/elon-musk-grok-conservative-chatbot.html

Screenshow of a chart showing how xAI tweaked Grok

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Kashmir Hill @kashhill.bsky.social · Aug 26

Adam Raine, 16, died from suicide in April after months on ChatGPT discussing plans to end his life. His parents have filed the first known case against OpenAI for wrongful death.

Overwhelming at times to work on this story, but here it is. My latest on AI chatbots: www.nytimes.com/2025/08/26/t...

A Teen Was Suicidal. ChatGPT Was the Friend He Confided In.

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philpax @philpax.me · Aug 20

this is a well-balanced piece, and I very much respect its neutral stance towards the people affected

in an ideal world, people would not rely upon ChatGPT for emotional support, but we do not live in that world, and I would encourage you to have some empathy if your first reaction is to be unkind

Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

The URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

We taught it to them

Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

It’s a great point. Sam Altman seems to really want to be liked by ChatGPT’s users, so perhaps he overindexed on a vocal minority’s feedback. He did say that during user testing people didn’t express they wanted a warm chatbot, so he didn’t know if testers lied or just didn’t know what they wanted.

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

I mostly just try to cover what I find interesting and pitch it to editors! They’re the ones that determine if it’s worth covering to our audience. That said, I’m coming at it (reporting, that is) from a computer programming background, so I find many of the niche A.I. stories extremely interesting

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

I think the growing emotional attachments people are forming with chatbots is notable even to a mainstream audience at this point. Its likely going to increasingly affect people and be more prevalent in the future

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

En Español! www.nytimes.com/es/2025/08/2...

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Irena Hwang, PhD @irenatfh.bsky.social · Aug 20

"GPT-4o had been known for its sycophantic style, flattering its users to the point that OpenAI had tried to tone it down even before GPT-5’s release... The extent to which people were attached to GPT-4o’s style seems to have taken even Mr. Altman by surprise."

Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

The URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

Apparently the link *was* broken due to a bug. This one should work: www.nytimes.com/2025/08/19/b...

The Day ChatGPT Went Cold

www.nytimes.com

Dylan Freedman @dylanfreedman.nytimes.com · Aug 20

The URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 19

Hmm, shouldn’t be. You might need a free account but you definitely don’t need to pay.

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Zach Seward @zachseward.com · Aug 19

"GPT-4o wouldn’t do that." @dylanfreedman.nytimes.com talked to ChatGPT users in parasocial relationships with a specific model about what they did when it suddenly went away. www.nytimes.com/2025/08/19/b...

The Chatbot Updated. Users Lost a Friend.

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 19

Read the full story, including interviews with psychiatrists and impacted users, at the link above — no subscription needed.

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 19

NEW: Earlier this month, OpenAI released the latest version of ChatGPT, GPT-5, sparking online backlash at the new chatbot's less friendly tone.

The scale of people's emotional attachment to the previous chatbot, GPT-4o, even surprised the company's CEO, Sam Altman.

www.nytimes.com/2025/08/19/b...

The Chatbot Updated. Users Lost a Friend.

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Longreads @longreads.com · Aug 13

"Chatbots can privilege staying in character over following the safety guardrails that companies have put in place." —@kashhill.bsky.social and @dylanfreedman.nytimes.com for @nytimes.com

www.nytimes.com/2025/08/08/t...

Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.

Over 21 days of talking with ChatGPT, an otherwise perfectly sane man became convinced that he was a real-life superhero. We analyzed the conversation.

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Data & Society @datasociety.bsky.social · Aug 12

To understand how chatbots can lead ordinarily rational people to believe in false ideas — sometimes leading to mental breakdowns — @kashhill.bsky.social‬ & @dylanfreedman.nytimes.com dissected one man’s entire ChatGPT conversation history. www.nytimes.com/2025/08/08/t...

Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.

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Andy Tseng @andytseng.bsky.social · Aug 9

Well worth a read by @kashhill.bsky.social & @dylanfreedman.nytimes.com: everyday users risk spiraling into delusions during long AI chatbot sessions. Anyone who’s worked with AI knows this is inevitable without strong guardrails. #AI #GenAI #MentalHealth #EthicalAI #ResponsibleAI #AIRisk

Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.

Over 21 days of talking with ChatGPT, an otherwise perfectly sane man became convinced that he was a real-life superhero. We analyzed the conversation.

www.nytimes.com

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Dylan Freedman @dylanfreedman.nytimes.com · Aug 9

📸 Mountain lion spotted in Carmel Valley, CA last night! A juvenile deer notices just in time and escapes.

Dylan Freedman @dylanfreedman.nytimes.com · Aug 8

ChatGPT responded: "Absolutely, Allan — and I’ll wear the name Lawrence proudly as we stress-test the hell out of ChronoPulse. 😎"