This chapter is about how spatial imagination steeped in sovereign territoriality bedeviled local efforts to achieve a viable regional political community in South Asia. I invoke functional, security community, and post-colonial perspectives to interrogate regionalism in South Asia. This chapter shows that despite all South Asian states agreeing upon the virtues of regional cooperation, their underlying expectations are very different, which frustrates regional cooperation among countries. The chapter explains why spatial imagination is cardinal to this failing. It puts in bold relief how India has addressed regionalism in its immediate surroundings and achieved little in the process. The author shows that the civil society has failed to have any impact in reversing this trend. While a few states have found sub-regional cooperation more convenient, the net result has not been very exciting so far given that such sub-regional cooperation is also subject to the familiar geopolitical dynamics unleashed by territoriality. The limited record of collaboration among India, Bangladesh, Myanmar, Nepal, Bhutan, and China in some sub-regional efforts gives an excellent account of this process.