The Holy See has been a permanent observer at the United Nations since the 1960s and as such followed the phases and the end of the Cold War closely, with some voices arguing that Pope John Paul II was one of the driving forces in ending it peacefully. More than thirty years later, the Holy See continues to employ a Cold War rhetoric in its diplomatic communication, for example when depicting the Ukraine War following the Russian invasion. This article explores two aspects of Holy See diplomatic representation during and after the end of the Cold War to establish whether and how its understanding of the international society has changed in the last sixty years. On the one hand, it examines the diplomatic representation of the Holy See around the world (e.g., with which states and institutions does it maintain diplomatic relations; have there been ruptures?). On the other hand, it analyses the Holy See's diplomatic language (e.g., does it employ terms such as bipolar world, great powers, balancing?). The findings are then discussed to better understand the Holy See's diplomatic representation and what this might reveal about the international society.