The Slender Man, an online monster born to the internet in 2009, loves to live in the boundaries, specifically the boundary between the digital and the non-digital worlds. This chapter seeks to explore the full engagement of the community with the myth, analysing it structurally to understand the way, in which the narrative’s construction reflects the relationship of monster to society and society to itself. The sincerity in which the narratives are told, at first appearing intense, is actually a form of play, revealing a boundary blurring between play and non-play as well. While fully engaging in play, the community’s structured narrative is more than this: pulling them into a trapped world in which they play with death in the digital. The triadic structure of the Slender Man narratives reveals an anxiety to the community and their place within broader non-digital worlds.