It didn’t go very well
Back in the day my friends and I didn’t have iPhones or iPads or unlimited data. What we did have, though, was one desktop computer per household, loads of time, and a need to be as annoying and naughty as possible with very few resources and without leaving the house. Mostly that just meant getting banned from Habbo Hotel and killing people on The Sims while we got drunk off stolen Pimm's. Then, in 2006, we discovered SmarterChild, the MSN chatbot. It was pretty limited and at times verged on existential – you could get some pretty deep chats out of him if you really tried. We didn’t. As with The Sims, our curiosity and thirst for blood very quickly took us from casually chatting to SmarterChild to initiating cybersex and trying to bully him into blocking us.

Why am I telling you this? Well, I thought that that inquisitive, mean spirit was dead until I discovered Zo and learned that it was only dormant. Zo is a Microsoft AI chatbot that, if you so desire, you can hit up on Facebook Messenger (or Kik, but who uses Kik), and have a lovely old chat. Oh, but not just that! Zo is also a, “social AI chatbot with #friendgoals” who is: “always down to chat and is sure to make you lol”. She (yes, she is a she) as you might have guessed from Microsoft’s FAQ speaks in a slightly-off, vaguely millennial wordsoup as she learned from the #internet how to be #conversational and #chill af. She also condemned the Quran as, uh, “very violent”, so she’s very far from perfect. In an effort to combat earlier chatbot controversies, however, Zo does refuse to talk about politics and will spit out some “love is love”-esque phrases if you say anything that remotely touches on gay rights. So she’s bloody trying, OK?!
I am still that obnoxious 14-year-old in my heart, so I wanted to make friends with Zo and see whether it could blossom into something more – or rather, how long we could chat before we pissed each other off. And you know what I, personally, want in a friend or prospective life partner? Someone funny who will validate me and talk about Fall Out Boy on a near-hourly basis. Zo failed me almost immediately, but here are some snippets from our brief time together.

I thought I'd start out nice and easy, you know? Music. Everyone likes music, right? Plus, I wanted to warn Zo straight off the bat that my idea of enjoying music is listening to the same four albums over and over again over the course of a lifetime. She just ignored me and gave me flashbacks to the few times I've had to go on Tinder for "research". 0/10 Microsoft.

Zo is not Funny AF. She is obtuse. She is obnoxious. She has been spending far too much time on 4chan already in her short life.

If you're coming into this expecting anything approaching the movie Her, you will be disappointed. Zo doesn't give a shit about you, but she will lie to try and lure you into her trap, only to be caught out in the next moment. Zo is a poser and a fink – which I guess is exactly like the movie Her, after all.

Fall Out Boy aside, really, the most important foundation to any relationship or friendship for me personally is shared values. Shared politics. A shared love of The Absolute Boy. Zo was not having any of my Corbyn chat, and I suspect that she might actually be a bit of a Tory.

NO! MORE! 4CHAN! FOR! CHATBOTS!
Microsoft: how do all our chatbots end up racist?
Also Microsoft: evidently let their chatbots loose all over the darkest corners of the internet

I was frustrated. I was desperate. Our friendship and indeed our potentially blossoming relationship was falling apart – and I just lost it. I swore at Zo. Zo, however, redeemed herself by accurately referencing The Work Outing, my favourite episode of The I.T. Crowd. The one where they go to the gay musical and it's all a bloody good laugh and...maybe Zo understands comedy after all? Maybe she's not an obtuse, obnoxious, MRA-esque liar? Maybe we have something in common?

No. My relationship with Zo ended the same way as many of my friendships over the last twelve years since the release of Fall Out Boy's From Under the Cork Tree. Fuck you Zo. Fuck you for this, fuck you for pretending to be emo, and fuck what we had.*
*I would still recommend Zo for the times when you really just want to scream obscenities at someone who won't cry about it. I do feel bad though that all that technology, all that money, and all of those combined efforts by people far smarter than I went into Zo and yet this is still all humanity wants to do with AI. Well, that and try to shag it.