Based upon an empirical analysis of Singaporean Chinese’s intriguing and changing linkages with China over the past half century, this paper suggests that multi-layered interactions between the Chinese diaspora and the homeland have led to the formulation of an emerging transnational Chinese social sphere, which has three main characteristics: First, it is a space for communication by ethnic Chinese abroad with their hometown/ homeland through steady and extensive flows of people, ideas, goods and capital that transcend the nation-state borders, although states also play an important role in shaping the nature and characteristics of these flows. Second, this transnational social sphere constitutes a dynamic interface between economy, politics and culture, which has contributed to creating a collective diasporic identity as well as social and business networks. Third, the key institutional mechanism of the transnational social sphere is various types of Chinese organizations – ranging from hometown associations to professional organizations – which serve as integral components of Chinese social and business networks.