This chapter examines the corollary converging and diverging interests of host community members and volunteers to illustrate how questions of authenticity, self-development and cross-cultural exchange emerge within the complex cultural politics of volunteer tourism. Despite the new contexts in which volunteer tourism emerges, the traditional Western tourists' "search for authenticity" in seemingly pre-modern or pre-capitalist peoples and places has not lost its power. Rather, it is re-framed as the authentic cross-cultural encounter. This narrative of "pre-modern" authenticity is ironically developed within the development project in volunteer tourism. Authenticity has been a central concern in the Anthropology of Tourism for over four decades. In its persistence, volunteer tourism has been re-framed as an authentic cross-cultural encounter. Cross-cultural experiences in volunteer tourism have the potential to both justify and overshadow or interrogate broader structural inequalities that the experience is based on. Volunteers become increasingly confident throughout the volunteer tourism experience.