This nascent desire drove him across the globe at this impressionable age to study philosophy in Europe for eight years. His guide and mentor in those formative years was a Hungarian philosopher, whose insightful and enlightening discussions on philosophy ensured that the young Rupesinghe earned a solid grounding in Western an Indian Philosophy. This timely exposure to the Western culture at a very early age armed him with much-needed subjectivity of his own Sri Lankan culture. Gaining an insight into different schools of thought allowed him to perceive transparently the shortcomings in his native land.

In the meanwhile, he continued his academic growth by obtaining a Degree at the London School of Economics and received his Doctorate from the City University - London. Over time, he went on to become a Research Fellow at the Agrarian Research and Training Institute, Colombo, (1971-1973) and was appointed Director of the National Youth Service Council.

It was but natural that one of Rupesinghe’s core concerns was human dignity, or the lack of it, which he witnessed during the ethnic riots of 1958 in Sri Lanka, where a close Tamil friend and his family were killed brutally. Little did he know that this experience would shape the trajectory of his entire life as his philosophic bent of mind grappled with the injustice and the discrimination of minorities in the north and east of the island.