Personal diplomacy refers to a situation where a nation’s top leadership and senior officials actively involve themselves in the diplomatic efforts of their government and directly communicate with other countries’ leadership and senior officials. Despite its highly personalized domestic political system, the literature lacks an analysis of Greek foreign policy in terms of personal diplomacy and this study aims to be a first step in this direction. After providing a conceptual analysis of this concept which has started to become popular in the discipline of international relations, the study will show how personal diplomacy was successfully adopted by Venizelos towards the Turkish government in the interwar period and why this practice failed in successive decades despite repeated attempts to solve problems with Turkey through leadership communication. The hypothesis of the study is that personal diplomacy is a necessary but not sufficient element for sincere dialogue between Greece and Turkey, yet it may constitute an effective method to overcome misunderstandings between the parties.