The current heightened sensitivity around history, colonisation and the aftermath of the socio-political and cultural ethos of the world can create in many people the fear of cultural appropriation and misrepresentation. This fear can affect the ability to imagine and play in certain learning settings, especially in devising performances, socially engaged theatre, and other arts-based explorations. However, what happens when participants choose not to engage due to the abovementioned fears? This paper considers the differing ways in which fear of cultural appropriation and misrepresentation deterred students from learning while teaching in Canada.