As the Portuguese settlement of Macau came to occupy an important position in the emerging global commercial web, it became a crossroads where peoples from disparate parts of the world—in particular, Portuguese and Chinese—came together to engage in a profitable trade. Historians have often treated Macau as a prototypical example of cross-cultural interaction and hybridity: a point where East and West converged and blended; an “Intercultural City,” in the words of one scholar. Yet, the notion of Macau as a place of intermingling and blending obscures some of the ways in which Macau's inhabitants did not quite “come together.” Here, I focus on the asymmetry in linguistic communication that developed in Macau: members of Macau's Portuguese mercantile elite did not become fluent in any of the Chinese dialects, and did not learn how to read or write the Chinese script, while a number of the Chinese who came to live in Macau—whether as merchants, tradesmen, labourers, servants, or slaves—became proficient in Portuguese. Drawing from a range of sources in Portuguese and Chinese, I argue that this asymmetry developed for several reasons, including the difficulty of the Chinese language, the Chinese government's approach to foreign relations and maritime, and the political and economic power of the Portuguese within their Lusophone enclave. I also consider how the Portuguese reliance on others for assistance with cross-cultural communication—most notably, Jesuit missionaries and Chinese jurubaças (interpreters)—shaped the evolution of the multicultural community.