The presentation adopts a comparative perspective to the problem of British Cold War cultural diplomacy, through an analysis of the Foreign Office and the British Council’s objectives and policies in Czechoslovakia and Kuwait during the 1960s. Drawing on an array of primary source material, we explore British perceptions of the challenge of conducting cultural diplomacy in these two different states. On the one hand, there was Kuwait, former British protectorate and recently wealthy microstate, with a broadly pro-Western government but an intelligentsia and youth population strongly swayed by Arab Nationalism and anti-Western. Czechoslovakia presented an opposite picture, with a Communist government (albeit an ultimately radically reformist one) and a vigorous local interest among the young and educated in British culture and educational opportunities. The paper illustrates the different ways in which the Council conceptualised its missions in Kuwait and Czechoslovakia, and how such conceptions were translated into policy. It shows that there was a greater emphasis on culture – from modern painting exhibitions to ballet – in the more ‘familiar’ territory of Czechoslovakia compared to Kuwait. In both countries there was a determined effort to exploit local interest in educational opportunities in the UK and to use English Language Teaching as a practical demonstration of Britain’s goodwill and potential as an aid to personal and national development.