While recent developments in artificial intelligence (AI) and robotics may reign in a new era in human-machine interaction (HMI), we can draw on a wealth of existing and evolving experiences and intellectual adventures rooted in philosophy and science, technology, and society (STS) studies to inform our theoretical and practical engagement with this new phase. In this paper, we propose widening the set of stakeholders and tools deployed to explore pathways to navigate the risks and opportunities these developments entail, how the narratives we use in describing and envisioning shape how we think about HMI, and how specific philosophical frameworks can be well suited in envisioning the complexities of human and AI/Robotics collaboration.