Ellsworth's article entitled "Why doesn't this feel empowering? Working through the repressive myths of critical pedagogy" raises issues about the complex dynamics of implementing critical pedagogy in real classrooms, and the difficulties and paradoxes of putting the empowerment rhetoric into practice. This article analyses the challenges of putting the rhetoric of web-based intercultural dialogue into practice, based on my previous experience as a facilitator and trainer/coach-of-facilitators of such a programme: one which involves web-based video-conferencing dialogue between students from the Arab/Muslim world and those from the US/West.