The internet and the digital world at large has been promised to bring efficiency, understanding and happiness to humankind. However, what we see are filter bubbles, polarization, weaponized social media and cyber wars. Instead of tech-utopia there has been a fracturing of reality. In this article, we describe an approach based on anticipation studies, futures-oriented dialectics and cultural and societal studies on post-digital to combat this fracturing. Using this approach we ask what kind of assumptions are made about the futures of the digital world and what are the socio-cultural-technical tensions between these assumptions? By using a past but still topical depiction of the future of online communication as a guide we explore some assumptions and the underlying tensions and illustrate our framework. We conclude with a discussion on how to move forward with building an ethical and aesthetic relation to realities in the digital realm and in the intersection between digital and physical.