The aim of this paper is to discuss and examine the regional projects of institutionalism in Europe and Southeast Asia. The main focus is on Myanmar, a regional ‘outcast’ whose membership in the Association of Southeast Asian Nations in 1997 has helped it to gain international legitimacy and be able to stand relatively strong against Western sanctions. The military regime is riding on the wave of ASEAN norms and a communitarian culture. The question remains as to how long the country can continue to do so. A rather skeptical view is emphasized on the ‘ASEAN Way’ in dealing with the military regime, and for the overall political dialogue with the European Union. Many ambitious objectives such as sovereign equality in institutionalism are widely questioned, and the European Union has gone against many of its treaties in order to keep its relationship with Southeast Asia. The paper puts prominence on the political and security relationship rather than on the economic aspect, which has been far more successful. The role of values and the human rights debate will be highlighted and described as the greatest obstacle for any future political cooperation.