Macro sociopolitical milieu and micro interpersonal interaction are intimately connected, since transformation of one’s cultural identity is realized in the ways in which one interacts with others through words. This paper outlines the modern Taiwanese cultural landscape — engendered through political, social, linguistic changes, as well as modern technological advances — which gives rise to new forms of talk. Political openness and rising local consciousness, changing social values to prioritize the self, emphasis on multiculturalism and multilingualism, revolution in modern technology and communication devices, and so on, have contributed to ways of language use diverging from traditional Chinese cultural values. No longer a subdued, other-oriented, reserved society subscribing to traditional cultural norms, Taiwan has embraced new forms of talk as it stands at a turning point. In light of the need for a contextualized and updated understanding of Chinese communication, as in the case of Taiwan, it is argued that many taken-for-granted assumptions endorsed through lens of “collectivism,” must be scrutinized and re-examined.