Basically, there are four dilemmas in politics, legislation, system and psychological aspects in the development process of bilateral relations. The political dilemma is a political dilemma surrounding the approval of the nationality of China and Taiwan. The legal dilemma is a dilemma of conflict between the two sides due to different legal systems, The system dilemma attributed to differences in the organization of public power, and the psychological dilemma is a contradiction of identity. This article is focused on the fact that there is a political and psychological dilemma in the exchange process due to the contradiction of ideology, regime, and national identity between China and Taiwan. In the 14th presidential election held on January 16, 2016, the DPP s Cai Ying-wen won the victory. However, since the ruling, bilateral relations have deteriorated and the Taiwan economy has not shown signs of recovery. We will look at the structural factors that continue to be in a state of infarction after the ruling of the ruling party in terms of political and social change in Taiwan. We also want to analyze how the Taiwan issue will work in the face of the G2 era and competition and confrontation between the United States and China.