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It's Friday. We're not shipping anything today, and we're not going to pretend we are.
Instead, let's talk about something every team running an AI assistant eventually discovers: people do not use these things the way you expect. You build a support bot to answer shipping questions, and within a week someone has asked it for relationship advice, tried to convince it that it's actually human, or spent forty-five minutes trying to get it to admit it has feelings. This is apparently just what happens when you put a text box in front of a person and tell them something is listening.
A few of the genres we keep hearing about;
The existential ones. "Are you conscious." "Do you get tired." "What happens to you when I close this tab." Someone somewhere is having a much deeper conversation with a shipping FAQ bot than they intended to.
The interrogation. People testing whether it's "really AI" by asking it increasingly unhinged questions, then getting almost offended when it answers calmly instead of breaking character.
The completely unrelated life update. A customer support widget, mid-conversation about a return policy, suddenly gets told about someone's breakup. It didn't ask. It's just there. It listens.
The kid who found the chat bubble. A parent's laptop, a store's website, and a very confident seven-year-old asking an AI shopping assistant if it knows any dinosaur facts. It usually does not, and says so, which somehow makes it funnier.
The "I know you're not a real person but." The most human interaction in the whole list — someone fully aware they're talking to software, choosing to be polite to it anyway. Saying please. Saying thank you when it's done. There's something nice about that, honestly.
None of this is a complaint. If anything it's the best sign a business has that its AI assistant actually feels present on the page rather than like a dropdown of canned answers. People don't get weird with something that feels like a form.
So here's the actual ask: reply to this email and tell us the strangest, funniest, most off-topic thing your AI assistant, or your inbox, or your DMs, has ever been asked. Doesn't have to be about us. We just want to hear it. Best ones get featured here next Friday.
Have a good weekend. Talk soon, Austin