In this chapter, the authors draw upon our experience as researchers within the Playful Engagement project, aimed at identifying the efficacy of applied theatre practices as a means of enhancing the quality of life for individuals living with mid to advanced stages of dementia, to consider how normative assumptions within applied theatre need to be re-evaluated in such contexts. Critical hope, as an idea, draws on the concepts of critical theory emerging from the Frankfurt School and the work of Freire. It can be summarised as ‘an act of ethical and political responsibility that has the potential to recover a lost sense of connectedness, relationality, and solidarity with others’. In some cases, this rewriting process informed a shift in relationships and/or care, which are, in themselves, representations and expressions of critical hope. Critical hope in a care home setting, therefore, is about a conscious acknowledgement of the challenges that the sector has in delivering ‘quality’ care.