Can artificial intelligence create entertaining storytelling for the rest of us?In the future the media landscape, where we will be immersed, would be completely different from today’s media ecosystem. Emerging trends shows the arise of machines in the form of robots and AIs as companions and intellectual workers. AIs and robots will interact with us through virtual reality experiences and smart environments.Conversations with Alice is a virtual reality application where the content is completely generated by algorithms. The app explores 3 different media, sound, visuals and text, all coming from different algorithmic and generative sources.A dialog between chatbots is the narrative voice that walk with the player in immersive imagery that evokes the dreamy atmosphere of Carroll's Alice in Wonderland. The landscape is an algorithmic modification of panorama images taken by a robot, while the soundscape is generated parametrically.The audience is called to step into a mechanical world that feels poetic and has the aesthetic of a dream. The project wants to interrogate new possibilities of entertainment and challenge the role of AI as a new factor in determining society’s future power structure.Is AI smart enough to create compelling stories? Do we still find interesting visuals in a VR setting that are created by algorithms?Will automatically generated content have a political weight? Can we forecast the strategies that organizations will use to control AI?These are the open questions that the project explores and hopefully they will be answered, implicitly or not, by the voyagers of the surreal world of Conversations with Alice.