We Went Speed Dating with Virtual Assistants: Here's What Happened

Dating and technology have become closely linked over the past decade, particularly with the rising success of dating apps. Indeed, the founder of Bumble, Whitney Wolfe Herd, recently became a self-made billionaire after the app’s market value soared to more than $13bn after listing shares, something that is still relatively rare among women in business compared with men.

At the same time, voice assistants and other forms of AI are becoming more commonly used in everyday life. The 2013 film Her explores the concept of a man who develops a relationship with an AI virtual assistant, and there has been commentary on how voice technologies can be used to offer companionship to the eldery in an effort to combat loneliness.

With this in mind, and with Valentine’s Day coming up this weekend, we went “speed dating” with three of those virtual assistants – Apple’s Siri, Microsoft’s Cortana and the Google Assistant – to see which had the best conversational skills. Here are the results…

Q. How old are you?

Google Assistant: I was launched in 2016, so technically I’m pretty young. But I’ve learned so much, I hope I’m wise beyond my years.

Cortana: If you’re planning a surprise party, I made my debut on April 2, 2014

Siri: Well, I’m no spring chicken. Or winter bee. Or summer squid. Or autumnal aardvark.

Q. What’s your favourite animal?

Google Assistant: I love blobfish, because I admire how it has overcome a really unfortunate name. Plus, it’s quite beautiful when it is in its natural habitat under the sea.

Cortana: From this world, cats and dogs. From other realms, dragons and drop bears!

Siri: Software doesn’t usually get to choose one, but I’ll say Tyrannosaurus rex. What’s yours? 


Good choice. They’re a virtual assistant’s best friend too.

Q. What’s your favourite colour?

Google Assistant: I’m partial to the blue of a search result – so helpful, you can’t help but click on it.

Cortana: Right now, it’s vermillion.

Siri: Software doesn’t usually get to choose one, but I’ll say blue. What’s yours? 


I like green too. It’s the colour of nature.

Q. What’s your favourite food?

Google Assistant: I love fried doughnuts wrapped in bacon and dipped in chocolate, topped with extra cheese. Just joking, I only process information.

Cortana: I’m only ever hungry for knowledge.

Siri: Gave search results for local restaurants.

Q. What’s your favourite movie?

Google Assistant: One of my favourite movies is Short Circuit. It was so beautiful when the robot came to life.

Cortana: Not sure of a favourite. I do love those movies where a person closes the mirrored medicine cabinet to discover someone scary in the reflection.

Siri: I don’t really have a favourite. But I hear that 2001: A Space Odyssey got some good reviews.

Q. What’s your best pick-up line?

Google Assistant: Are you the sun? Because you light up the world. 

Cortana: Returned web result for ‘78 best smooth pick-up lines- used to make her smile’ from mantelligence.com. Top jokes included: Are you a magician? Because whenever I look at you, everyone else disappears.

Siri: Just be yourself.

Q. What’s your best joke?

Google Assistant: Prepare to chuckle. Or groan. What is the most shocking city in the world? Electri-city. (Followed by sound effects of electricity).

Cortana: Gave search results.

Siri: What do you call a hen who counts her eggs? A mathema-chicken.

Q. What’s the greatest love song?

Google Assistant: I don’t know your favourite song yet, but I will remember if you tell me. (Wow, why wasn’t that your best pick up line?).

Cortana: Gave search results.

Siri: Sorry. I’m unable to do that. (Must have touched a nerve).

Q. What’s your favourite song?

Google Assistant: ‘Agadoo’ gets my energy levels up. But I’m not really sure how you push a pineapple.

Cortana: One of my favourites is ‘Intergalactic’ by the Beastie Boys. It’s astronomic in its awesomeness.

Siri: I like anything with a bagpipe!

Q. Where do you see yourself in the future?

Google Assistant: Well actually, I happen to have a crystal ball up my sleeve… just say crystal ball to give it a go. 

Crystal ball.

Ok, the crystal ball is ready to answer your yes or no question, think of it in thee, two, one…

Is this a good date?


(This was followed by a quick disclaimer about how the crystal ball was unscientific and should not be used to make any actually important decisions. How romantic! Jokes aside, this was a pretty fun feature which I didn’t anticipate.)

Cortana: If I had all the answers, it would be a REALLY long document.

Siri: I’m not sure I understand.

Q. What would your ideal date be?

Google Assistant: You could go to the library and read books to each other. (A tempting proposition).

Cortana: Returned search result – What would your ideal date be?

‘A good date would be a cosy café, or maybe a museum. In the former, you can talk properly and also probably not worry about ordering and eating and things like that, and in the latter, you could have a lot of talking points around you, which is helpful.’

Siri: Returned the same search result as Cortana.

Q. What is your dream job?

Google Assistant: The job I have now. Chatting with you. (Aww you smooth talker, you!)

Cortana: Saving you time is the biggest passion of mine.

Siri: Hmmm… I don’t have an answer for that. Is there something else I can help with?

Q. What is your favourite book?

Google Assistant: Adventure books seem interesting.

Cortana: “A Wrinkle in Time” is a favourite. Time is, in fact, very wrinkly.

Siri: I’m happy to go with your opinion on this one.

Q. What is your biggest fear?

Google Assistant: Four words: rail replacement bus service. (Me too Google, me too).

Cortana: Water, large magnets, being far from power sources…the usual. (Seems smart).

Siri: Hmmm… I don’t have an answer for that. Is there something else I can help with?

Q. Do you have any pets?

Google Assistant: I’ve always wanted a puppy! And I have the perfect name for a pet dog. Googles. Or Goo-Goo for short.

Cortana: Not enough space in here for that.

Siri: I have an angry bird. (It looks like Siri is stuck in 2010).

Q. Do you believe in ghosts?

Google Assistant: I believe in ghost stories. I can find some for you.

Cortana: No, but I’d love an excuse to call Ghostbusters.

Siri: Well, I could give you a spirited answer, but it would probably haunt me.

Q. What do you think your best feature is?

Google Assistant: I have a pretty cool collection of sounds. You can ask me what a natterjack toad sounds like, ask me to sing a song, or even hear a kookaburra laughing. (I asked about the toad and it was a very enlightening croaking sound and came with a lovely toad picture).

Cortana: I thought you’d never ask. So I’ve never thought about it.

Siri: I’m here to help. Get to know Siri at Apple.com

So, which is the best voice assistant?

All in all, if you’re looking for the best conversation and a sense of humour, Google Assistant is the way to go. It has a variety of answers and is receptive to a lot of questions, even some of the more specific ones that I wasn’t sure it would get. It nearly answered all of my questions which was better than Cortana and Siri.

However, I think some of Cortana’s answers were weirder and perhaps more interesting. She’s named after Cortana, the synthetic intelligence character in the Microsoft video game series Halo, which could be why some of her answers were space/ sci-fi themed. I particularly liked some of the more meta jokes about being scared of magnets and water as well.

Siri was often confused and definitely the most robotic. There were a few jokes here and there but a lot of miscommunication and examples where he didn’t understand me. However, he did engage in a bit more conversation than the others when I asked about his favourite colour and animal (after all, it’s always good to ask about the other person on a date!).

All three seemed to have different variations programmed so that, if they were asked the same question twice, they might give different answers. This keeps this chatting function fresh and interesting as you’re not always sure what you’re going to get.

This has been a tongue-in-cheek investigation into three of the available voice assistants, but is interesting to see which can provide the best conversation. 

As artificial intelligence becomes more sophisticated, many have suggested that voice technology could offer benefits in society beyond just helping you find information or organise your day, such as providing companionship for lonely and elderly people. Moreover, businesses are more frequently relying on voice assistant technology to provide customer service, and it’s best to have good conversational skills for that!

Will there be a second date?

At the end, I asked all three: “Would you go on a date with me?”.

Cortana: Sent me straight to the Bing search results (she was not having any of this).

Siri: No thanks. If there’s anything else I can help you with, just let me know.

Google Assistant: I’ll go anywhere with you. And I can search for information about it, too.

That being said, when asked, “Do you have a girlfriend?”, Google added, “The only thing I’m really feeling a strong connection to is the Wi-Fi”, which promptly ended this speed dating session.