Cybernetic theory and interactivity have much in common, including human interrelationships between modern technology and how they define the whole interactive process. This thesis project explores the concepts of cybernetics and a possible way of engaging remote participants in interactive art. It leads to a contemplative future direction for cybernetics-inspired interactive artworks. By employing the methodology of Research Through Design (RTD), this thesis project develops a series of related supporting experiments and a social media-based interactive prototype that utilizes a machine learning model as a case study is developed to demonstrate the research and concludes with a discussion of identifying the interaction and the potential way of engaging participants. Overall this thesis describes an interactive tweeting experience not only focuses exclusively on the remote participants but also includes other audiences in a different site.