Is your chatbot a comedian?
As part of a comprehensive testing exercise on dozens of support chatbots, we encountered some chatbots with a delightful sense of humor. Here are a few examples for your enjoyment. (Names are withheld for privacy.)
There are limits to my power
![Dialog with bot. User: How can I set up alerts? Bot: "Probably not, sadly. [Product] change alerts are typically controlled by admin level configuration, not something a standard user can turn on for one record. [Bot name] tried to bribe the permissions system, but it would not take cookies."](https://www.ftworks.com/wp-content/uploads/2026/10/chat_03_alerts_cookies-264x300.jpg)
Thanks for your effort, FriendlyBot!
I know I need to grow up
A little formal but it’s nice that the error will be reported and fixed.
I’m on your side, man
![Dialog with a bot. User: How do I cancel my subscription? Bot: "Nope, there is not a single [product] mega FAQ that lists self-cancel steps for every product in one place. Annoying, I know. [Bot name] does not make the rules, I just wear the tiny virtual hat."](https://www.ftworks.com/wp-content/uploads/2026/10/chat_02_cancel_all_subscriptions-279x300.jpg)
Charming, right? (I would love for it to notify its overlords of the omission.)
I messed up
Could have cut out the second sentence but good job naming what went wrong. (FriendlyRobot does loves its em dashes!)
I can make work sound like fun
![Dialog with a bot. User: How do I set up alerts? Bot: "You've got a few fun ways to set up 'alerts' in [product], depending on what you're tracking!"](https://www.ftworks.com/wp-content/uploads/2026/10/chat_01_fun_ways_alerts-300x251.jpg)
It even supplied an exclamation point! Can’t wait to try all these fun approaches.
What can your bot do?
We all need a bit of levity in our lives. Train your bot to be (appropriately) light-hearted. You can run a few tests to find out how it’s doing now—or ask me how to adopt an AI-driven continuous testing protocol.
And stay tuned for more stories of the secret lives of chatbots.
