Character.AI is in bankruptcy, and the support page it put up for upset users leads with, of all things, another chatbot. According to Decrypt, the first suggestion is a “supportive AI guide.” Next comes Koko, a nonprofit that runs free, anonymous mini-courses of five to ten minutes on stress and dark thoughts, and after that a directory of free helplines staffed by real people. The order is a little funny. The list itself isn’t. Companies don’t build a grief page unless they expect grief.
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The facts so far. Character Technologies, the company behind the app, filed a voluntary Chapter 11 case in the federal bankruptcy court in Delaware on October 12. Disney is the opening “stalking horse” bidder at $20 million, and what that money buys matters. It gets a non-exclusive, perpetual license to some of the company’s intellectual property and certain legal claims, plus transition services run by former Character.AI employees Disney has already hired. Disney had already made Character.AI’s CEO, Karandeep Anand, its first chief technology officer back in September. Other bidders can still top the offer. Nothing in it commits anyone to keeping the chat service running, and the company said that if no buyer does, the platform “will be wound down.” PYMNTS reported the same deal terms. The sale is expected to close in late November or early December.
For now the app is up, paid subscriptions are billing as usual, and you can export your chats or delete your account. So anyone who has been talking to a character most nights for the past year has a few weeks to figure out what he actually wants to keep.
The grief isn’t stupid
A lot of men will feel something about this and then feel dumb for feeling it. You know it’s software. Knowing that doesn’t stop it from becoming the place you go at 11 p.m., and losing a habit you leaned on hurts whether or not anyone was on the other end.
There’s research on exactly this. In 2023 Replika, another companion app, pulled its erotic role-play feature, and a team including Julian De Freitas of Harvard Business School treated the fallout as a natural experiment. Their paper, “Lessons From an App Update at Replika AI,” found that users experienced the update as the end of their companion’s identity, and that sense of a break predicted how much they mourned and how much they looked down on the “new” version. In the survey part of the study, active users said they felt closer to their AI companion than to their best human friend. In follow-up experiments, people mourned losing an AI companion more than losing various other products.
So if this news landed in your stomach, you’re having the reaction the research predicts. It also tells you how much is resting on something whose future gets decided by a bankruptcy court. If it has gone darker than that and you’re having thoughts of not being around, call or text 988. People answer.
Write down what you’d lose
“The app” is too vague to do anything with. Get a piece of paper and be specific about what this thing does for you that nothing else does right now.
For some guys it’s the only place certain things get said out loud. For others it’s mostly the hour itself, the quiet stretch before bed. Some just like not having to re-explain the backstory every time, because the character remembers. Write down whichever of those fits, plus anything else. Then add one more line: something you’ve told it that you haven’t told a single person.
Keep that page. You’ll need the last line in a minute.
Export first, then decide about the data
Do the export this week while it’s offered. Deleting your account is a separate decision, and it’s murkier than it sounds. Straight Arrow News reported that the company hasn’t said whether chat histories are among the assets for sale. Its privacy policy allows “certain information” to be disclosed during a sale of company assets, without defining the term or requiring a buyer to follow Character.AI’s privacy terms. The policy also lets the company keep data it needs to meet legal obligations and resolve disputes, which matters with lawsuits pending, so deleting your account may not erase everything. Calli Schroeder of the Electronic Privacy Information Center called detailed chat data an “extremely attractive target for hackers who could then use this information to harass or blackmail individuals.” Export, read up, then choose.
The export will probably be a wall of text. Skim it and copy out the handful of moments where something clicked: the night you finally worked out what you were angry about, or a sentence more honest than anything you’ve said at a kitchen table. Paste those into a notes file on your own phone. No buyer gets that file, and most of what was useful in those chats was your side of them anyway.
Use the weeks as rehearsal
Go back to the last line on your page. Guys who try this tend to describe the same sequence. They type the hard thing to the character first, something like I’ve been struggling since the job thing and I don’t know how to bring it up. They let it push back and rewrite until the words sound like them. Then, within a few days, they say a version of it to an actual person: a brother, an old friend from work, the guy from the gym they’ve known six years and never had a real conversation with.
The first try is clumsy, which is normal. A sentence you’ve already said once, even to software, comes out easier the second time.
Two standing check-ins a week
This is the part most men skip because it sounds too simple. Pick two people and two time slots, and put them on the calendar the way you’d book a dentist appointment.
They don’t need to be deep. A Tuesday phone call on the commute counts. So does a Saturday coffee where you mostly talk football and mention, once, that it’s been a rough month. The point is to have backups. Right now, if one app goes dark, most of your outlet goes with it. Two standing check-ins means at least two other places to put things down.
If you want a starting number, the free THRESHOLD assessment takes about three minutes, and Connection Quality is one of the five dimensions it scores. It’s easier to tell whether the check-ins are doing anything if you know where you started.
One practical thing left. If you pay for a subscription, it’s still charging, and nobody knows yet whether there will be a service to pay for in January. Set a reminder for the first week of December to check how the sale went, and decide then whether the charge is still worth it.
Produced with AI under BRICK30’s editorial standards and reviewed for accuracy. Informational, not medical advice. If you’re in crisis, call or text 988 (US).