Southeast Asia's location as a crossroads between East and South Asia, marks it as a region deeply entrenched in difference, with a history of complex identities. Apart from indigenous cultures that have survived the tides of change, there are several deeply embedded cultural influences from near and far that constitute what is local. Education that engages with this complexity mustnegotiate the borderlines of culture that contribute to how Southeast Asian nations apprehend themselves, and in relation to each other. In this article, I propose a critical approach to "regionalist" education in Southeast Asia by engaging with issues of culture in teaching and learning contemporary theatre. I deploy Henry Giroux's border pedagogy as a working frame to grapple with difference in Southeast Asia, with particular reference to his view that borders are expressions of power that need to be interrogated through pedagogies of difference. I then describe and analyse how the learning process and assessment tasks created for an undergraduate module on Contemporary Theatre in Southeast Asia at a teacher-education institution in Singapore offer students a space to work with pedagogies of "difference" and "discomfort" and reconfigure the boundaries of their identities and communities as potentially local, regional and global.