This chapter responds to the poly-life-crisis of the Anthropocene, as this requires a transformation of how we live as humans in ways which can engage care for life to disrupt current prevailing life-destructive practices in the context of modern mainstream techno-bureaucratic schooling. Departing from Jane Bennett’s suggestion that you have to love life before you can care about anything, this chapter explore questions of how educational events can foster new opportunities to imagining, sensing, and attuning to traces of life and co-existence to learn from. Inspired by posthuman relational approaches to knowledge, education and research, this chapter visits empirical materials based across different educational contexts and describes how the authors have experimented with a speculative research practice called life-friendly walks to provoke and explore the pedagogical event of becoming life-friendly. Inspired by this, the chapter unfolds four new concepts around life: the life-wound, life-forgetfulness, life-sensibilities and life-friendliness. The chapter discuss how this as a speculative research practice of life-friendliness, can work as a walkable story that helps didactical reflections around the role and form of care for life in an Anthropocene age.