This paper argues that the South Korean government’s policy during the entire post Cold War period, from Roh Tae-woo’s administration to the current Lee Myung-bak administration, did little to resolve the issues pertaining to the conflictual North-South relationship. This is because the problems of today, including the North Korean nuclear problem, were largely the consequences of the failure of Nordpolitik. North Korea’s nuclear ambition as well as its go ahead started in the very sensitive entry period in to the post Cold War era (1988 – 1993). Despite all its claimed success in dealing with China, the Soviet Union, and the rest of the formerly communist countries, South Korea’s Nordpolitik failed to penetrate North Korea to produce any foundation on which the problem of division could be dealt with. In fact, President Roh Tae-woo’s Nordpolitik had the impact of solidifying the partition of the Korean peninsula, isolating the already fragile regime in the North – pushing it in to the embrace of nuclear arms. Thus, the questions to be asked here are: What when wrong? And, if any, what can the South Korean Government salvage from such an experience? Upon addressing these questions, the paper delves in to West Germany’s successful policy of Ostpolitik to seek out lessons from it.