Using action research methodologies, this study investigated whether selected Shakespearean stories could stimulate Socratic discussions on the decisions made by the characters. Then, in parallel with the topics on the Personal, Social and Citizenship curricula, the students philosophised on alternative ways of thinking and acting and vicariously develop their own social and moral reasoning. The research design was based on the eclectic ‘bricoleur’ model developed by Kincheloe and Berry (2004) and was supported by both quantitative and qualitative analyses. In order to capture the complexity of measuring the impact of Shakespearean stories a three-tiered research template was designed. Based on the response to neo-Kohlbergian conundrums discussed in the thrice-yearly home interviews, the informers’ personal and social development (PSD) was assessed using Kohlberg’s ‘six stages in moral reasoning’ as a measuring stick. Then, having triangulated the PSD variations from other sources, ‘partial connections’ (Law, 2007, p.155) were sought between the Shakespearean stories used in the action research and the informers’ PSD.