The research question will consider how artificial intelligence technologies support written content creation in interactive artworks to improve and understand audience engagement. The consequent analysis of the audience interaction with the application can expose limitations of the technology that, if addressed, can improve the quality of the human-computer interaction, the trust of autonomous systems and the sharing of personal data and experiences. This analysis can also help understand how people attach meaning and value to digital interactions with autonomously generated written communications and better develop autonomous systems. Another objective of using AI in an art context is to investigate the technology with a critical approach without the constraints of commercial driven decisions and with an openness of unexpected outcomes proper of art exploration and audience interaction. The research aims to understand the dynamics of conversation between a human and an artificial intelligence chatbot in an artistic context that might deliberately position the conversation in an unusual situation, perhaps not comfortable, or highlights aspects usually ignored in similar commercial applications. As art can inspire us to see things differently and encourage exploring new territories, the goal is to communicate a critical message embedded in the art installation and learn more about the technology from the audience interaction with the artwork. This critical approach to technology is partially the foundation of several Blast Theory artworks that often combine live and online engagement with their audience, investigating the tension between the very private and the very public, between direct physical experience and a digital interaction through the Internet and new technologies.