This paper aims to analyze the asymmetric dilemma facing the Philippines and China in the South China Sea tensions. Among American East Asian allies, the Philippines seems to stand on the frontline between two rival powers, the United States and China. Since the US declared its Pivot to Asia policy, the Philippines’ foreign policy towards China has become assertive and sometimes appears reckless with some military adventures against Chinese maritime patrols and naval ships, which also further forced China to take a tougher foreign policy against the Philippines. Considering the distinctive asymmetric indicators between China and the Philippines based on military forces, economic capacity, territorial size, and population, the aggressive policy behaviors that the Philippines and China have been displaying against each other cast an inquiry on what drives the two countries into head-to-head collision. While China as the larger power vis-à-vis the Philippines as the smaller power in the relationship has aimed for control and domination of their disputed territory, the Philippines’ drastic defiance has also led to China’s irritation and possible frustration. Furthermore, the US’ renewed attention to Asia has caused shifts of asymmetric bilateral dilemma to triangular entanglement between the US–China–Philippines. It is vital therefore to pay attention to the asymmetric interaction of states and their varying views in order to find possible solutions to the SCS tensions.