This paper draws on a study of a larger investigation involving 17Á18-year-old students engaged in enactive role play in the Second Life virtual world. The study is set in the context of a subject, General Paper, offered at the pre-tertiary level in Singapore to promote critical thinking and argumentation. Central to the study are the questioning types adopted by students in a simulated negotiation based on the context of globalisation and its implications on an international level. Students enact the roles of lead negotiators for parties in a dispute concerning a fictitious group of islands, which aimed to join the community of regional and international democracies after decades of totalitarian governmental rule. The findings based on an in-depth examination of a focused group of participants indicate a range of questioning types in evoking participant response with varying levels of assertion. Direct and rhetorical questions occur more frequently compared to those which require further work in internal processing and strategising in the use of particular discourse features such as reformulation, internal scaffolding, indirect and mirror-effect questioning types. The examination also extends to the role of questions in extended questionÁresponse sequence chains of virtual dialoguing. The pedagogical implications of enactive role play for developing students' questioning skills are discussed.