From being a love that dared not speak its name to one that is legally recognized by many countries today, same-sex acts and relations have indeed undergone a remarkable transformation in terms of how they are perceived and, consequently, regulated. Yet, globally speaking, this transformation is taking place unevenly as many countries continue to criminalize homosexuality and the commission of same-sex acts. In Asia, a region that has traditionally if misguidedly been seen as more sexually conservative than the so-called 'Wild West,' the debate over the acceptability of homosexuality rages on. As three of Asia’s most economically developed, cosmopolitan, and Confucian Chinese-majority societies, Hong Kong, Singapore, and Taiwan nevertheless treat homosexuality very differently; sex between males continue to be a crime in Singapore while Taiwan appears poised to be Asia’s first country to legalize same-sex marriage. This paper seeks to examine the domestic and external factors that combine to produce in each country a unique set of dynamics and logics governing public policy and discourse about homosexuality. It is argued that one-party hegemony in Singapore, transfer of Hong Kong’s sovereignty to China, and Taiwan’s insecure international status vis-à-vis China represent the primary factors mediating state regulation of homosexuality. This paper also includes a survey of traditional Chinese, Confucian, and Japanese attitudes regarding homosexuality, as well as the implications of Singapore being the only de jure independent sovereign state among the three case studies.