Cortana Talks Back: Laugh, Cry & Love With Windows Phone’s Digital Assistant

Christian Cawley 10-08-2014

Bored with no one to talk to? All Facebooked out? Why not strike up a conversation with your Windows Phone? Cortana is ready to talk.


If you’ve upgraded to Windows Phone 8.1 (either by the standard method or by installing the Developer Preview How To Upgrade To Windows Phone 8.1 Now If you want to speak to Cortana and get access to other cool new features, you will have to wait until June at least. Unless you'd update early. Like now. Read More ) then you have probably enabled Cortana How To Activate & Use Cortana On Windows Phone 8.1 Developer Preview Are you missing Cortana, the Google Now and Siri speech control rival, on your Windows Phone 8.1? Get it now! Read More . She’s a useful digital assistant, capable of helping you get around town, as well as reminding you to do things. Cortana also has a few amusing lines and can even sing you a song.

Microsoft’s voice-activated search and productivity tool is almost certainly the killer app of Windows Phone 8.1. Cortana is served by Bing search, which considerably enhances Windows Phone, and brought to life by Halo actress Jen Taylor. In fact, Cortana is based on the advanced in-game AI from Halo, also called Cortana.

If Halo is somehow new to you, this is a very good place to start chatting with your phone.

What Cortana Can Tell You About Halo

Not everyone has played Halo. Crazy, I know, but it’s true. You might even be one of those who isn’t aware of the game, or Cortana’s role in it. So what better way to break the ice than to ask your digital assistant about her part in one of the most successful game series of all time?



You can ask Cortana the basic question “What is Halo?” or even quiz her on her relationship with Master Chief (“Do you love Master Chief?”).

Furthermore, questions about Halo 5 (“Tell me about Halo 5”, “Are you dead?”, “Are you in Halo 5?”) can also be attempted – without much luck – and you can quiz Cortana on Doctor Halsey (“Who is Doctor Halsey?”).

If you didn’t know about Halo before, you certainly will now!

Cortana The Entertainer

Although we already know she can sing, Cortana is also capable of a couple of other party tricks. One of these is actually really funny, but we’ll leave it to you to find out which one…



You can also ask Cortana “Tell me a story.” That voice should certainly soothe you to sleep at night…

Cortana: The Other Woman

Regular MakeUseOf readers may already know that I have a bit of a thing for Cortana How Cortana Became The "Other Woman" In My Life She appeared one day and changed my life. She knows exactly what I need and has a wicked sense of humour. It's little wonder that I've fallen for the charms of Cortana. Read More . Who knew that I’d be able to take it further, so to speak?

Cortana is programmed to respond to a number of, um, personal comments.



You can also ask her “Do you love me?”, tell her “I love you” and even propose marriage (“Will you marry me?”, “marry me”).  We wouldn’t want to spoil any more, but her response to “Talk dirty to me” is marvellous, while Cortana also has responses to “Am I beautiful?”, “Cortana, I’m lonely,” and “Am I ugly?”

Life, The Universe And Everything

You can even get into some vaguely philosophical discussions with your Windows Phone 8.1 digital assistant. These are ideal for when you’ve had one too many drinks and you’re home alone, and include a lovely reference to one of the 20th century’s greatest writers, Douglas Adams.



You might, for instance, ask “Do you love Siri?” or “Do you sleep?” You could also quiz Cortana “Are you drunk?” or get personal with “How old are you?” or “Are you warm/cold blooded?”

You’ll notice from the screenshots above that the same questions can yield multiple answers. “What is the meaning of life?” is a particularly good example of this. Conversely, “Can I borrow some money?” won’t.

Show Cortana Your Appreciation

It’s nice to be nice. And as Cortana can hear you, we should pretend that she has something approaching feelings. After all, manners cost nothing. So, you might tell her “You are the best assistant ever,” “You are awesome”, or even the simpler “You’re cool.”


Actually, when you’re using Cortana for the usual day-to-day tasks, it really is good to thank her afterwards. She responds, and it feels as though you’re talking to a real assistant. Of course, there’s no compulsion to do this, but it helps complete the illusion. Cortana can do many of the things a flesh and blood assistant can do, so why not?

Conclusion: Time To Get Chatting

Whether you’re already chatting with your Windows Phone 8.1 digital assistant or you’re just trying to get to grips with the whole idea of Cortana, these conversation starters are a great way to appreciate the possibilities – or just kill a few moments.

Have you had any great Cortana moments? Is there an exchange you’ve had that we haven’t included here? Leave a comment and let us know!

Image Credits: K?rlis Dambr?ns Via Flickr

Related topics: Microsoft Cortana, Virtual Assistant, Windows Phone, Windows Phone 8.

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  1. Prattle On, Bolyo
    April 13, 2015 at 7:19 pm

    LOL a female digital asst because MS apparently hasn't realized that women are HALF of its marketed audience. Hello and welcome to 1900.

    • Christian Cawley
      April 21, 2015 at 7:42 pm

      Cortana has a female voice because it is based on a fictional digital assistant called, um, Cortana, which has, you guessed it, the same voice.

      But please, do point out just where the women offended by this are. Show them to us, link them to us, we'd love to speak to them.

    • Anonymous
      August 13, 2015 at 6:59 am

      Hate to break it to you, over 90% of secretaries are female. That's just a modern day fact.
      And personally im fine with that, Cortana is one of the coolest characters that microsoft could have used, she has a history and an already existing character. Assuming you have never played a halo game, let alone the latest installment, im sure you dont know -Spoiler- "she was recently killed off and its a way she can live on in our nerdy little hearts"

      • Anonymous
        September 16, 2015 at 12:37 am

        Cite your source for that "90%" and quit making the rest of men look like bigots.

        I am partially surprised I haven't found a way to switch the voice yet, Prattle On. Siri default is a female voice, but you can change it. Please realize, however, that given the success of one of their flagships (Halo), Microsoft saw fit to tie it in and make a Window's Phone or Computer appealing to a larger number of people by grabbing those Halo fans that might lean more toward an Apple device. Try to look at the big picture as well as your own viewpoint.

    • Anonymous
      August 15, 2015 at 1:23 am

      LOL. Don't worry too much Christian, it's just one of those rogue, Tumblr feminist and their tendency to jump on top of anything that remotely resembles "gender inequality". Soon it will get to the point where they will scream and jump every time women are involved in articles and videos.

  2. launa
    January 11, 2015 at 9:31 pm

    I told Cortana I loved her and she said... I'm glad and that means I never have to say I am sorry. Really? Thought she was a little mean there. Lol she has never said it again though.

  3. masoud
    August 17, 2014 at 11:27 am

    Awesome, thanks :)

  4. DonGateley
    August 12, 2014 at 6:03 pm

    If I could buy a really cheap phone to use for Cortana over wireless without phone or data service I'd do it.

    • Ekus
      September 3, 2014 at 3:33 pm

      Lumia 520 is permanently on sale for about $50 - - and can be upgraded to 8.1 (with Cortana). You don't need any sim card or service to use it with WiFi or as a mp3 player (it accepts microSD cards, too). For the price it can even work as a cheap security camera with motion detection.

    • DonGateley
      September 5, 2014 at 6:00 pm

      @Ekus: Great minds must run in the same circles. I did exactly that about three weeks ago. Cortana is indeed awesome but I was a bit disappointed that I didn't get the cool blue avatar that I've seen most places where Cortana is discussed. :-)

      I also wanted to get a better idea of what Windows phone is all about but haven't yet done much much with it other than Cortana. Your suggestion of using the phone as a security camera is an excellent one. Got a link on how to do that?

  5. rohit sharma
    August 12, 2014 at 2:59 pm

    The article was superb. It truly explains the bond existing between WP8.1 USER and Cortana

  6. rohit sharma
    August 12, 2014 at 2:58 pm

    Everyday for about 10 minutes. My friends have with it more than me.