The division in the Korean peninsula has lasted more than a half century, and the people on both sides have become quite different in their values, beliefs, behaviors, and lifestyles. As the two sides have increased their exchanges and communications for the last several years, the biggest challenge Korea and its people face is: "How should human relationships be rebuilt after suffering from chronic conflicts between adversary states?" This article considers track two diplomacy/people-to-people dialogue as a response to this question and reviews the issues and obstacles related to initiating such a dialogue.