This article looks at the evolution of EU-ASEAN relations, covering legal framework and policy change. By examining major legal instruments, it illustrates how the legal framework governing the EU-ASEAN relation becomes deeper by adding Cooperation Agreements and Partnership and Cooperation Agreements with individual ASEAN member countries to the 1980 EC-ASEAN Cooperation Agreement. It also exposes the dynamic nature of EU-ASEAN relations spurred by the Global Europe strategy and highlights the EU’s ambition to play a greater role in South-East Asia through its Partnership and Cooperation Agreements with individual ASEAN member countries. It then assesses the shift from region-to-region approach to individual ASEAN member country approach and probes into future directions of EU-ASEAN relations.