The examination of a mid-18th-century biography about a significant developer of Ojibwe and Cree-based syllabics is the starting point for an interrogation of socio-historical cultural cohesion in Canada. The textual creole of syllabics, used widely in business and commerce, provides clues to the dynamics of cross-cultural linguistics. In this essay, I use a discussion of the influence and crucial role played by the creole language Papiamentu in the southern Caribbean island of Curaçao, and its elevation to a core language of instruction in the post-secondary system, as a means to better understand the necessity for greater intercultural dialogue in Canada's post-secondary environment. Through this discussion, I draw on the combined views of Paulo Freire, Michel Foucault, and Herbert Marcuse to illustrate ways in which Canadian learning institutions could do a more effective job to support, engage, and promote cross-cultural dialogues in the classroom. Notwithstanding policy and funding for greater cross-cultural discourse in Canadian post-secondary classrooms, teaching institutions continue to focus less on engaging in necessary difficult discussions that address diversity and far more on a Eurocentric, Westernized education concentrating on the application of dominant cultural values. In spite of the Truth and Reconciliation Commission's call for Indigenizing the academy and the federal government's creation of an Aboriginal Languages Act, Canada's higher-education realm does little to explicitly promote cross-cultural thinking in the way that creole would. A lack of culturally elaborate thinking is especially pronounced in areas that should touch all aspects of Canadian life, such as curricular initiatives for reconciliation. Instead of relegating such courses to focusing solely on these issues, an integration strategy is necessary. A more effective approach would be the inclusion of diversity-focused work across disciplines within the regular curriculum in order to generate a more effective intercultural developmental capacity across the curriculum.