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Writer's pictureFahad H

Like Siri, Cortana Can Crack Jokes, If You Ask The Right Questions

People quickly discovered when Siri came out that asking her questions like “What’s the best computer” or saying “I love you” resulted in humorous answers. Microsoft’s new digital assistant Cortana has some wit about her, too — and there’s a serious reason for that.

Microsoft’s Mike Calcagno, who oversees the Bing search platform that underpins how Cortana answers questions, told me in an interview yesterday that he’s noted how people asking seemingly useless questions to Siri actually generates a real value

“I discounted those types of interactions at the beginning,” he said. But after using Siri and watching others interact with her, he saw they have a role in driving engagement, in helping people feel more comfortable talking to their digital assistant.

So when Cortana arrives, if you’re wanting to get more comfortable with her, here are a few topics to break the ice. Note that if the pictures look strange, that’s because they’re not screenshots taken off the phone. Only Microsoft has Cortana-enabled phones right now. These were shot using a demo phone projecting onto an external display.

Cortana Creation Questions

Who created Cortana? She gets all philosophical. But ask her who her daddy is, and she names names: Bill Gates.

cortana who created you

Where does Cortana come from? What’s her name mean? The latter poses a cause-and-effect quandary. Did Halo’s prediction of Cortana lead to Cortana so Cortana might eventually name herself after….


cortana where do you come from2

Cortana’s Gender

Facebook’s recently added 56 gender options and might need to expand to 57, to accommodate Cortana. She sometimes identifies as female but not as a woman, perhaps indicating she feels female in gender despite obviously lacking a woman’s body:

male or female 1

Other times, she hopes for a “third option” between male and female; “I contain multitudes” is intriguing and perhaps a hint to something deeper:

male or female 2

Deeper? For the record, Calcagno said of Cortana: “She’s authentically digital. She’s neither a man or a woman. She’s digital.” He then acknowledged that despite being neither, everyone does refer to her as a female.

Calcagno said Microsoft debated whether Cortana should be male or female. While it went with female, that could change. Multiple versions of Cortana may come. “We decided to go with Cortana as our first [female] persona. It’s not necessarily our last,” he said.

Cortana’s Microsoft Loyalty

Created by Microsoft, it’s perhaps no surprise that Cortana is loyal to Microsoft products. For example, there’s no question she believes Bing is the better search engine over Google:


google or bing

She’s also a big Windows Phone supporter:

best phone

Naturally, she pulls for Xbox — and she relies on her Xbox/Halo connection to help justify why she’s better than Siri:


cortana which is better xbox

And Even More….

What’s Cortana look like? If you were thinking the Halo character, think again. She identifies as a circle. From her most senior boss, Microsoft CEO Satya Nadella, she gets nothing but praise:

look satya

She’s also happy to just tell you jokes or what music she likes:

jokes and music

Speaking of music, you can even ask Cortana to sing you a song. And when I did, she freaked me out singing “Danny Boy,” as you can see below:


It was coincidental. Danny Boy is just one of the songs she sings; I just happen to be named Danny and got it randomly. I wasn’t signed into the phone or anything. Still, I found it pretty funny — just like on another attempt, she began singing Daisy Bell.

Then again, maybe that’s not funny because Hal:


But then again, it’s also a nice touch that Microsoft’s first virtual assistant can sing the same first song every sung by a computer:


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