Reformation era has rolled for fifteen years and during that time various steps to democratize the institutions and procedures of Indonesian politics have been conducted with a number of real transformation. However, the idea of deliberative democracy (dmeokrasi permusyawaratan) based on the principles of Pancasila is still far beyond expectations. This situation should be corrected. Deepening and extensioning democracy need to be done to establish a healthy democracy with cultural ideals. The biggest challenges to establish such democracy is to develop a cultured democracy and developing conducive cultural values to the development of democracy. Learning from the experience of Indonesian history and the successful examples of other countries, this paper tries to review how these biggest challenges should be responded.