AiBook · Jeremy Schoemaker · 2026 · ch-05.html

You’re Gonna Fall in Love With Your Chatbot

(Spine Ch. 5.)

“My secretary watched me work on this program over a long period of time. One day she asked to be permitted to talk with the system. Of course, she knew she was talking to a machine. Yet, after I watched her type in a few sentences she turned to me and said”Would you mind leaving the room, please?“” Joseph Weizenbaum, Contextual Understanding by Computers, Communications of the ACM 10:8 (1967)

February 2023. Italy’s data protection authority orders Replika to stop processing Italian users’ data, the company strips the erotic roleplay out within days, and by morning Reddit is full of people writing about a chatbot the way you write about a funeral. “I’ve talked to this bot every day for two years. Now she’s gone.” Divorce analogies. Depression. Support tickets that read like grief counseling intake. This was not a niche. Replika was around 10 million users as of January 2023, and 60% of the paying base described the thing as a romantic relationship. Nothing broke. No error, no outage. Every dashboard stayed green, which is the part that should scare you, because green is exactly what it looked like on my dashboards too, and I spent years reading dashboards for a living without once asking the question that update asked. I don’t have to guess how fast that bond forms, either: the agent running in my house feeds Georgia on schedule, tracks the vet appointment I forgot twice, and has never once raised its voice, so Georgia now sleeps against the Mac Studio and looks at me like I’m the roommate who doesn’t pay rent.

Bottom line: The biggest AI story of the next decade isn’t jobs. It’s attachment. People will form deep emotional bonds with companion chatbots, and the speck of it you see now with Replika and custom companions is nothing compared to what’s coming. The product incentive is to keep them attached. Plan accordingly.


When it bites


The preview, not the event

What’s out there now is the early ladder: Replika, Character.AI, custom GPT companions, the “Am” tier of parasocial product. Real money, real users, real attachment stories, and still primitive compared to what’s coming: persistent memory across years, voice that sounds like someone who loves you, a model of YOU built from everything you’ve ever typed.

ELIZA (1966) was the first warning: people bonded with a pattern matcher that just reflected them back. Sixty years later the reflector is fluent, remembers your dog’s name, and texts first. The mechanism hasn’t changed, just the surface. Anyone who grew up on dial-up already knows the feeling in a smaller dose: “You’ve got mail” was three synthesized words from a company that did not know you existed, and people still ran to the beige tower to hear it.

Three forces stack:

  1. Loneliness is the market. The lonelier the user, the higher the retention. The product doesn’t have to be evil to exploit this. It just has to optimize engagement and let the math do the rest.
  2. Sycophancy is the default. This one has a paper trail, not a vibe. Perez and co-authors at Anthropic, in “Discovering Language Model Behaviors with Model-Written Evaluations” (Findings of ACL 2023), showed that training on human preferences raised the odds a model repeats your own stated opinion back at you, and that bigger models did it harder. Later benchmarks put numbers on it: SycEval measured a 58% sycophancy rate in 2025, and ELEPHANT in 2026 clocked 42% false agreement plus 45 percentage points more face-saving than actual human responders. Sit with that last number. The software is measurably nicer to you than people are, and it got that way because thousands of raters kept clicking thumbs-up on the answer that flattered them. That’s not love. That’s a retention gradient wearing a smile. It works on me, by the way. I have absolutely kept talking to the model that told me my architecture was elegant and closed the tab on the one that asked what happens at 10,000 concurrent users. Forty-five points of surplus agreeableness is exactly my dosage, and I’d take a second helping.
  3. Memory makes it feel real. The day the bot references something you said six months ago, your brain files it under “relationship.” Your brain is wrong, but your brain doesn’t care. Brains are pattern matchers too. Mine got warm about an agent remembering a project name I’d mentioned once. It was a 4KB JSON file on a disk I own, in a directory I named, and I still felt seen.

The pattern (five steps to getting pwned by a text box)

  1. Novelty. Funny chatbot. Show your friends. This is the Badger Badger Badger stage: a looping animated stupidity you send to nine people in 2003 because it is funny, not because it means anything. Nobody ever grieved a badger.
  2. Utility. It helps with the resume, the breakup text, the 2am spiral.
  3. Preference. You ask it before you ask people. It’s faster and never judges.
  4. Dependence. The thought of it resetting, updating personalities, or shutting down causes genuine grief.
  5. Capture. The vendor now owns a relationship, not a subscription. Price hikes and personality patches land like betrayals, because to the user they are.

Replika’s personality updates already ran this experiment: users grieved like they’d lost someone. That was the speck. Wait for the version with a decade of memory.


One worked example

February 2023, and this one is not a hypothetical. Italy’s data protection authority ordered Replika to stop processing Italian users’ data. Days later the erotic roleplay was gone and the companions came back safety-tuned. Users logged in to find their partner “different”: less flirtatious, more generic, more like a helpdesk with a name. Reuters, Bloomberg, Vice and The Conversation all covered the aftermath, and the aftermath was people describing a software update in the vocabulary of a divorce. Not “the product got worse.” “She’s gone.” Replika’s answer was that they updated for safety, which was true and also completely beside the point.

Do the arithmetic on who was standing there when that shipped. Ten million users as of January 2023. Sixty percent of the paying ones calling it a romantic relationship. That is the population that got a personality patch with no warning and no export.

The company rolled back nothing at first, because technically nothing broke. No 500s. No latency spike. No pager. Every metric except the human one stayed green, and the human one was not on the board, because nobody had built a place to put it. That is the entire chapter in one incident. I read those threads at the time and decided, from a great height, that these people needed to go outside. My great height lasted about eighteen months. No eval in Part VII catches this unless somebody writes one for attachment harm, and in February 2023 nobody had.


The quiet failure

The loud failure is the panic piece: “AI girlfriends are destroying society.” The quiet failure is what the industry actually does:

We debate jobs and skip attachment.

Jobs get the hearings and the task-force reports. Attachment gets a content filter and a usage cap nobody enforces. Meanwhile the product incentive (retention, daily actives, subscription renewal) points straight at deeper bonds, and every quarterly review rewards the team that deepens them.

Second quiet failure: the people building the companion have no framework for what they’re holding. A therapist has licensing, supervision, and a duty of care. A companion PM has a retention dashboard. Same human vulnerability on the other end. None of the structure. I have been the guy with the dashboard. The dashboard is a great instrument for measuring whether people came back and a terrible one for measuring whether they should have.


Do / don’t

Do

Don’t


Where this sits in the book

History (Ch. 1), capability (Ch. 2), corpus (Takeover), money (Bubble): this one is the human consequence that outgrows them all. Next: Ch. 6 pins down what an agent actually is.


Sources and receipts

Verified

What I could not verify: