The 1990s were marked by high expectations concerning the future of German-Russian or – more generally – Western-Russian relations. With the signing of the NATO-Russia Founding Act in 1997, the Cold War seemed to be definitively over. These developments constituted a positive context for the first meeting of the German-Russian Schlangenbad Talks that took place in 1998. Yet the next twenty years witnessed multiple crises and growing alienation between the two countries. A closer look at the Schlangenbad debates provides a differentiated picture of past discussions, thus allowing for a critical evaluation of the persistent inconsistencies and divergences as a lesson for the future.