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Emerging from Portuguese colonialism and Indonesian occupation to become one of the newest states, Timor-Leste is an interesting example of modern nation-building. Geographically, Timor-Leste is located in the area covered by the Association of Southeast Asian Nations (ASEAN). In such context, Timor-Leste has a strong claim to belonging to Southeast Asia. Timor-Leste nevertheless has not yet been admitted formally as a member despite its application for membership in March 2011. This paper locates Timor-Leste in a broader context of their construction of regional identity and as part of Southeast Asia. Drawing upon the constructivist approach, this paper suggests that the complexity of Timor-Leste’s regional affiliation with ASEAN is made more challenging with its quest to assert itself as a nation-in-the-making.