This work is intended as an analysis of possible links between educator and philosopher Paulo Freire’s thinking on dialogue, and the Art of Hosting (an international community of dialogue-based practitioners) as an approach to ‘hosting conversations that matter’.  This study was conducted by thoroughly reviewing Freire’s Pedagogy of the Oppressed, as well as conducting a literature review of a selection of his other works, and the analysis and commentary of other authors on Freire’s thinking. In order to gain a strong understanding and perspective on the Art of Hosting (AoH), the author turned to the few academic articles that have been written on AoH, as well as reviewing multiple handbooks produced to accompany AoH events around the world, examining the various online sites related to AoH, and the related blogosphere. Finally, the author conducted six semi-structured interviews with self-identified Art of Hosting practitioners using questions influenced and inspired by Freire’s views on dialogue. The result of this research brought the author to delve into a personal exploration on how her professional practice as a facilitator offers her an opportunity to directly, and indirectly, address the societal issues about which she is concerned, and how she is influenced and inspired by both a philosophical grounding in the work of Paulo Freire, and by the shared assumptions she encounters in the Art of Hosting community.