Humans make sense of language in context, bringing to bear their own understanding of the world including their model of their interlocutor's understanding of the world. In this talk, I will explore various potential risks that arise when we as humans bring this sense-making capacity to interactions with artificial interlocutors. That is, I will ask what happens in conversations where one party has no (or extremely limited) access to meaning and all of the interpretative work rests with the other, and briefly explore what this entails for the design of language technology.