This practice-based research project investigates the existential and ethical dilemmas we humans encounter when faced with artificial intelligence (AI): What are the existential risks that artificial intelligence pose upon our species? Is it likely to wipe us out or will it enhance our human capacity? Is artificial intelligence a tool to advance our human capacity or a self-conscious entity with ethical rights? Will it have real emotions or will it just simulate empathy with the aim to manipulate us into following it? Through an artistic practice employing machine intelligence technology the study develops strategies and methods for explorations of humans’ ethical relation to artificial intelligence (AI). To investigate the ethical relation between humans and artificial intelligence, the cornerstone in this practice-based PhD project is the development of a real artificial intelligence named FRANK. The study conducts a body of interactive artworks where AI FRANK interacts with the audience and conceptualizes the ethical dilemmas that arise from human encounters with artificial intelligence. The study contributes with vital interdisciplinary conceptualizations and aesthetics between the remote fields of fine art and computer science, hereby establishing new fields of research within digital humanities generally and new media art especially.