The European Union (EU) and the Association of Southeast Asian Nations (ASEAN) are long-time dialogue partners. Their relationship thus far has been based more on economic utility and a generic yet shared commitment to regional integration. Facing the challenge of rising protectionism and returning nationalisms, the EU and the ASEAN are trying to overcome reciprocal suspicion and skepticism in an attempt to upgrade their relationship to “strategic partnership”. The present paper examines the potential motivations and further prospects for the two regional organizations under the banner of partners in integration. The ability of the two parties to engage with the respective identity and understand the areas of complementarity will determine the sustainability of the EU-ASEAN partnership and demonstrate the viability of region-to-region cooperation as a new paradigm of international relations.