How can we understand German-Russian relations since German reunification? Both the geopolitical positions of the two states and the political and economic ties between them have been transformed over the past twenty-five years. This paper will argue, however, that the role of the two countries’ leaders in shaping these relations has been surprisingly important. Building on the tradition of “first image” analysis in international relations, this paper shows that, along with larger political and economic trends, personal relations between these leaders have helped to set the tenor of bilateral ties. When the leaders were able to build trust and personal friendships, relations improved. Yet more recently, since 2012, relations have soured sharply. While there are obviously larger reasons for this, more negative personal ties between leaders have also played an important role. In short, just as issues of trust and friendship matter in personal ties, they also matter in International Relations.