An important aspect of ICT, identified 25 years ago within the user interface design community, is dramatic interaction: The deep engagement promoted by digital technologies that can be better explored by adopting a conceptual framework traditionally used to describe and study theater. This framework offers a wider perspective that demonstrates a deep connection between the qualities of our hyper-connected era and drama as an art of representing action. These concepts transcend the prevailing technical mentality when addressing ICT. They imply that we all participate as “interactors” on the “onlife stage” where other agents (either humans or computer-controlled) are also present. By promoting deep experiences, the hyper-connected environment in which we live in, changes our metaphysics and self-conception. A dramatic framework can explain the power of ICT and help us work towards the development of an equilibrium both personally and collectively: When used to enrich our experiences and extend our agencies, ICT can be considered as an enhancement of reality. When, on the other side, they are used to promote a false reality experience, they should be rectified. Important ethical and anthropological concerns are framed on the same philosophical ground as ancient drama. Ancient drama was a major pillar of Ancient Democracy and served the need to educate citizens with empathy in order to participate as responsible actors in decision making processes.