The Canadian public largely understands reconciliation as the harmonization of Indigenous–settler relations for the benefit of the nation. But is this really happening? The Theatre of Regret asks whether reconciliation politics will ultimately favour the state’s goals over those of Indigenous peoples. Interweaving literature and art throughout his analysis, David Gaertner questions the state-centred frameworks of reconciliation by exploring the critical roles that Indigenous and allied authors, artists, and thinkers play in defining, challenging, and refusing settler regret. Through close examination of core concepts in reconciliation theory – acknowledgement, apology, redress, and forgiveness – this study exposes the deeply embedded colonial ideologies at the root of reconciliation in Canada.