This article is based upon research into a participatory Theatre in Education (TiE) programme that toured the West Midlands in 2009, funded by the UK's PREVENT initiative intended to counter the radicalisation of young British nationals by extremist political groups. The article provides a summary of the TiE programme and then presents quantitative data to demonstrate its success in terms of its ability to both provoke and entertain the young audiences whom it engaged with. The article then goes on to examine qualitative data gathered from two contrasting schools in an attempt to theorise why and in what ways it was successful as both a social exchange and an aesthetic event. In this the authors draw heavily from a recent work by Richard Sennett and propose that the programme constitutes the kind of dialogic encounter and civil exchange that he suggests we need in order to foster forms of cooperation and dialogue within the social and cultural complexities of the modern world. At the heart of this dialogue, we suggest, is the playful charm of actor-teachers and the productively cool dynamic they can bring to bear when working with highly emotive and politically charged issues. (Contains 2 tables and 11 notes.)