Since the end of the Cold War, almost all of the ROK governments have pursued their own versions of diplomacy toward the north, ‘so-called Northern Diplomacy or Nordpolitik.’ Despite gradual progress achieved up to now, there has been found no break-through stride. This paper tries to figure out the problems and contradictions intrinsic to it by exploring and examining the implications of the Roh Tae-woo’s Nordpolitik. In the late 1980s, the world witnessed sea changes: the rise of pragmatism among communist countries, the East-West détente and, finally, the demise of several communist countries. Such external developments drastically shifted the strategic environment of inter-Korean interactions in Seoul’s favour. Capitalizing on these changes, the Roh Tae Woo government charted a dramatic turn in South Korea’s diplomacy that came to be called Nordpolitik (Northern Diplomacy), a South Korean version of Willy Brandt’s Ostpolitik. The Roh government sought diplomatic rapprochement with communist bloc countries, attempted to pursue engagement with North Korea, and eventually, aimed to lay down the foundation for Korean unification. The Nordpolitik seemed to be successful. Between 1988 and 1992, South Korea expanded its diplomatic horizon to embrace communist countries, including the Soviet Union and China. However, its impact on the inter-Korean relationship was not as successful. On the contrary, Seoul’s diplomatic initiative ended up complicating inter-Korean conflicts alongside Pongyang’s nuclear hassle. This article argues that the Nordpolitk was not fully successful in engaging and reconciling with North Korea because it pursued mutually contradictory goals. It implies that the ROK’s Northern Diplomacy and its North Korea Policy should be decoupled; or that the concept of national unification may need to be redefined.