This chapter examines how engagement with transnational popular culture shapes individuals' sense of place in that imagined global order. Identifying the imagination as a key dimension of contemporary experience, it starts with an examination of the role of the media in shaping the awareness of the global. Media and globalization may have “partnered throughout the whole of human history”, but the nature of this partnership experienced a qualitative shift with the arrival of digital technologies allowing for “new forms of personal connection” and a deepening degree of connectivity on an increasingly global scale. While the digital age may signal a shift in the granular ways in which this imaginary is built and negotiated, this shift must be considered in relationship to this longer trajectory and within the broader context of historically dominant transnational media flows.