I made a generic tool to create such comedy-like / play discussions. It’s called Piece https://gitlab.com/raphaelbastide/piece
I used Piece later in other work, such as https://together.an.otherti.me/ (a discussion between Content and Style) and some quick (and incomplete) tests like that one, about a jealous bot https://raphaelbastide.com/piece/index

Remember AOL, AIM, ICQ, Yahoo, even Q-Link? We do too. That's why we're bringing them back.

Let's go back to the basics - when you hoped your modem would connect to the internet, when you changed your away message to tease someone, when you used to chat endlessly with people from all around the world. It's back, baby!

"Session is an end-to-end encrypted
messenger that minimises sensitive
metadata, designed and built for people
who want absolute privacy and freedom
from any form of surveillance."

see also http://omegle.com/

"When you use Omegle, we pick another user at random and let you have a one-on-one chat with each other. Chats are completely anonymous, although there is nothing to stop you from revealing personal details if you would like."

""Project Upstream;" a (harmless) bot system using AOL Instant Messenger that contacts two random people to engage in a completely random conversation."

a study of anonymized data capturing a month of high-level communication activities within the whole of the Microsoft Messenger instant-messaging system.

generates a 3D avatar (for widget use) from a photo of your face

a multi-networks IM that intends to be a social networks (chat) client too. interesting. similar to 8hands and flock

"Users will see their friends' faces, and by clicking on them will be able to get a list of that person's recently added Flickr photos, favourite YouTube videos, tagged websites, composed blog posts, updated Facebook status, etc."

3D chat with customisable avatars + community à la Myspace. You can buy plenty of "accessories" to customize your avatar, but get 1000 free credits (1$) when you register

see and chat with people who browse the same webpage than you