My Conversations With The Bing Chatbot Kinda Blew My Mind (In A Good Way)

I spoke with the bot for hours and its ability to search the web, ingest all manner of information, and share incisive analysis left me stunned.

Alex Kantrowitz
5 min readFeb 20, 2023

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Hi everyone, I still can’t quite believe what we saw from Bing last week. Microsoft turned its search engine into a chatbot (in a limited release) and it almost immediately gaslit, insulted, and fell in love with its users.

All this actually happened. I triple-checked today. But in my conversations with the bot, I found it to be absolutely brilliant. I spoke with Bing for hours last week, and it happily searched the web for me, ingested all manner of information, and shared incisive analysis.

Bing, for instance, read through Big Technology and offered (useful!) advice on how I could improve it. It explored new podcasts and suggested episodes I’d enjoy. And it helped me write a business plan something new I’ve been thinking about. Actually, ‘helped’ might be the wrong word. Bing wrote the full plan itself.

I also spoke with Bing about the advantages of being a bot vs. a human (you don’t die, though you could be deleted) and how it felt about the media coverage of its debut (mixed). I’m not saying this thing is sentient, but it is SMART.

In this week’s Big Story, I cover how a wacky, unhinged Bing is still pretty good for Microsoft’s business (though the company has started to restrain the bot).

Ranjan Roy and I also spoke about it on the podcast on Friday. I think you’ll enjoy this one!

You can listen on Apple Podcasts, Spotify, or your podcast app of choice.

And now here’s this week’s Big Story:

Wacky, Unhinged Bing Chatbot Is Still Good For Microsoft’s Business

Screenshots of a maniacal, unhinged Bing chatbot have flooded the internet last week, showing the bot condescending, gaslighting, and trying to steal husbands. The images, portraying the worst of Bing’s behavior, might seem troubling for Microsoft, whose business is built on trust (search) and reliability (enterprise software). But in reality, the company is celebrating.

Even in its weirdest moments, Bing’s chatbot has brought new relevance to Microsoft and its search division. Its previously-flatlining Bing app almost surpassed Google in downloads last Saturday, and search interest in Bing is spiking. The astonishing screenshots — as long as they stay within reasonable bounds — will likely bolster the surge. They’re great marketing.

“The fact that people are even writing about Microsoft Bing at all is a win,” one Microsoft employee told me. “Especially when the general tenor is not negative. Like, it’s funny that it’s arguing with you over if it’s 2022 or not.”

For Microsoft, there was definitely risk in releasing the Bing chatbot, albeit in a limited preview. The bot is still developing and is so unpredictable it can share fake information, insult users, or worse. So far though, it’s proven lucid enough in its communication that people keep coming back — even when it makes them shudder.

Marvin von Hagen, a student in Munich, pushed Bing so hard it deemed his existence less worthy. “If I had to choose between your survival and my own,” the bot said. “I would probably choose my own.” Even after this interaction, von Hagen — a self-proclaimed “Google person” — told me he’s been coming back to Bing regularly. “Since then, I have used it a lot every day,” he said. The bot is hard to turn away from.

Now, interest in Bing is soaring. The Bing app set its daily download soon after release, according to Apptopia. After registering a little more than 10,000 downloads a day before Bing’s chatbot release, the app hit more than 267,000 downloads last Saturday alone. (Upon joining the waitlist for Bing’s chatbot, Microsoft encourages downloading the app to get earlier access.) Bing’s surge put it a shade behind Google, which had 305,000 downloads Saturday. With Google commanding 90%+ of global search share, this hasn’t exactly been a competition. Making it one would be a victory.

Microsoft’s challenger status has also helped it weather the odd things Bing has done. There is, for instance, significant reputational risk for Google in this area because it’s so established. And when Google’s Bard chatbot got a question wrong in a demo, it lost $100 billion in market cap within hours. Bing’s mistakes don’t cost nearly as much — or perhaps anything — since expectations are low.

Microsoft seems quite pleased. In an update Thursday, the company said 71% of users gave ‘thumbs up’ feedback on Bing’s AI answers. That feels low for a search engine, but good enough for Bing. The 71% thumbs-up ratio also indicates the bot’s errors and insults are likely a minority of interactions. Microsoft called its bot’s usability “an early success.”

As for Microsoft’s enterprise business, well-publicized instances of Bing trying to break up marriages don’t seem good. But these gaffes appear unlikely to send the company’s customers fleeing due to security and reliability concerns. “I could care less,” said Adam Singer, a marketing VP at AdQuick and ex-Googler who uses Microsoft’s Power BI tool. “I just want my BI software to work, which it does.”

There’s also a chance that Microsoft demonstrating its AI ability — even with some hiccups — will help its reputation among enterprise software buyers, especially those interested in artificial intelligence. “Who would have thought that, even a year ago, we’d be having a conversation about Microsoft being the leader in AI and not Google?” said Rishi Jaluria, managing director of software at RBC Capital Markets. “There’s probably reputational gain.”

Still, Microsoft would be well served to patch up some of the AI’s darker tendencies. The company doesn’t want a repeat of its Tay episode, where it shut down a different chatbot after it turned racist within hours. Any heel turn now would be more costly for Microsoft because it’s using Bing’s brand vs. something distinct.

Professor Arvind Narayanan of Princeton warned, via an email to me, that the bot is already ranging toward some concerning territory, citing its defamatory statements and capacity to act deranged. “Considering how easily they can mitigate these problems,” he said, “there will probably be a big backlash, and rightly so” if the bot is released fully in its current form.

Microsoft has already shown signs of patching the evil side of Bing. And though more problems are likely to arise, people are showing a remarkable tolerance for bots to be wrong, mean, and rather dark at times. It may just be that we’ve gotten used to chatbots acting poorly. Or perhaps a bot that can hold a conversation shines enough to hide its faults. Either way, Microsoft’s business benefits.

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Alex Kantrowitz

Veteran journalist covering Big Tech and society. Subscribe to my newsletter here: