The Lost Art of Conversation

Published by:

Eran Soroka

This article is about my five favorite chatbots, and I’m not going to feature ridiculous statistics like 76% of consumers say they prefer messaging chatbots on Mondays if they live in Belgium and are allergic to wheat. Or that 72% of unmarried men ages 27-79 who wear Axe body spray had positive sentiment when chatting with a bot about insurance rates! We measure sentiment using our state-of-the-art sentiment analyzer 9000 algorithm and found that women named Mary are 98% more likely to consult with a bot on conversational components-built Messenger chatbot before buying a hummus flavored dildo.

Ok, maybe I made that last one up.

Instead, I’d like to talk about the lost art of conversation, and how (most) of the bots out there are missing the mark entirely when it comes to, well, conversation.

A two-way street

What is the art of conversation? Well, it’s literally a book by Milton Wright from 1936 which explains how to properly hold a conversation. He states that in a one-on-one conversation there are two subconscious aims: To get to know the other person and to reveal yourself.

So basically, a conversation is a two way street; The bot wants to “reveal itself” meaning it wants to promote a product or a service and, ideally, it should want to get to know the other person, ie the user.

But how many chatbots out there really care about getting to know the user? Not very many. Why? Because with the current tools in the field of conversational AI it is REALLY, REALLY hard to get to know a user. At scale. It requires a huge set of intents and understanding, memory and multi-turn capabilities.

Playing it (too) safe

Unfortunately, there are only a handful of platforms that offer multi-turn capabilities. There are also privacy concerns when it comes to remembering sensitive user information.

The possibility of a false positive or flat out error is just too much for most enterprises/brands to stomach. So most play it safe. They stick to the first of Milton’s aims and reveal themselves (Hey, I’m BOTBOT your digital pal! I can show you how to cook meth or help you pick out a gift for Father’s day!”) without ever daring to get to know the other person. Don’t believe me? Ask your bot this one question: “Ask me something about myself” and see what it answers

So I scoured the web, took some breaks to watch cat videos on YouTube, laughed at the idiots on r/whatcouldgowrong and spent a good hour researching the mating habits of Mallard ducks (holy crap, who knew ducks were so f&*&ed up) and then decided on the 5 chatbots that touch on Milton’s second aim; getting to know me, the other person.Mitsuku. The five-time Loebner award winning chatbot is a LOT of fun to chat with. She also does take an interest in the user. In the case of Mitsuku, she went 3-4 turns deep while maintaining context. Very impressive. There’s a reason why Mitsuku is considered the greatest conversational AI in the world. Mitsuku was built using AIML, one of the most advanced languages for developing chatbots.

Some more great reading

How Anna and Mitsuku helped me overcome loneliness
What’s the best way to humanize your chatbot?
Every word matters: the linguistic part of conversation design

Virtual Alan Turing

This relatively unknown chatbot is probably the closest thing to a competition that Mitsuku has. Alan took an interest in where I was from, asked me if there was anything worth seeing there and then asked if I had grown up there. It felt like a real conversation with a friend. The reclusive chatbot guru who programmed Alan uses conversational components (CoCo) to build out this surprisingly intelligent chatbot. One caviat, the virtual Alan Turing is NOT supposed to actually be Alan Turing, but he does know a lot about Mr. Turing’s life and accomplishments.


This two time Loebner award winning conversational AI designed by Bruce Wilcox and his wife Sue was programmed to try and pass the Turing test. It is a very interesting bot with a very strong personality. This is HUGE. I love a bot that has personality. While most enterprises and brands shy away from revealing anything other than a sterilized, helpful personality, Rose, like a real human, doesn’t feel the need to oblige me (the user). I actually liked that about her.

It’s not that she can’t ask me about myself (it’s clear that Rose has an advanced NLP and multi-turn capabilities) it’s just that she doesn’t want. As Groucho Marx once quipped, I don’t want to belong to any club that has people like me as members. I don’t want to talk to any bot that feels it has to be nice to me and ask me questions about myself.

Genius (Albert Einstein)

This webby award winning bot was rolled out on Facebook messenger by Nat Geo/360/i and developed by an AI company called imperson. It was meant as a way to promote the first season of Genius and brought Albert Einstein to life. This wasn’t as robust as the above chatbots (meaning, it couldn’t hold conversations on ANY topic); however, it was surprisingly interested in me as a user. It asked me for advice (Albert was caught in a loveless marriage to Mileva but was deeply in love with his cousin… and he asked me if I had ever been in a similar situation).

Some may argue that he was only really fulfilling the first aim of Milton’s conversation; he was only taking an interest in me so that he could promote the show. But I found several exchanges had no bearing on the show. For instance, he asked me if I had any pets and then told me about how important it was to be kind to animals


The Joseph Weizenbaum therapist bot from the 60’s only pretends to care about me but you know what? I’ll take feigned interest over no interest at all! Weizenbaum himself was surprised at how many people attributed human-like characteristics to Eliza. It just goes to show that Milton was right; people want to reveal themselves and while a conversation with Eliza feels a bit comical now, there’s no doubt that it touches on a key aspect of the human psyche: people just want to feel like they are not alone.

Special Honorable mention to the #freemurdoc chatbot (Murdoc Niccalz, Gorillaz)

I would have included him in the list but he doesn’t give a crap about me or any other user…

So why should YOU care about my five favorite chatbots? Well, it could earn you $5,000. Let me explain.

On December 10th, 2019 CoCo – Conversational Components will be holding a chatbot competition to find the world’s most human-like chatbot. The only criteria is that teams have to use one of their conversational components in their bot to be eligible to win the $5K prize. I was asked to judge the competition; After (unsuccessfully) trying to obtain bribes from the participants (it’s not too late, people) I’ve decided to stop trying and just judge the bots based on merit.

But what are conversational components? Conversational Components, or CoCos, are like reusable parts for bots. Or plug ins that solve a specific sub-goal in a conversation. So for instance, CoCo offers a scheduling component which you can plug in to your bot, and it achieves the subgoal of setting an appointment with a user (and then returns control to your bot). They even have an Eliza component available, so your bot can, well, parrot back info to the user in a way that feels like your bot cares.