Cultural diplomacy has long existed as a tool of international affairs. However, only recently have academics begun to assess its nature and impact. As compared to the ‘hard power’ of military might, the ‘soft power’ of cultural diplomacy has often been deeper, lasting, and persuasive. In the India—Pakistan context the potential of achieving peace through cultural diplomacy is great. India and Pakistan are connected through a shared history and culture, and despite the seven decades of hostility several joint initiatives have proven the strength of these connections. This paper traces several ways in which India and Pakistan have managed to keep connected, mainly through people-to-people contacts and initiatives, and posits several ways in which they can be developed further to usher in peace and stability in the South Asian region.