“Aspirational Intimacy” investigates the transformative potential ascribed to vernacular languages in the postcolonial era, examining affective investments in vernacular language use in public life. Turning to texts, theatrical performances, radio broadcasts, and cultural institutions in the Anglophone and Francophone Caribbean and their diasporas, the project provides an account of uses of vernacular languages in literature and politics to resist oppressive systems. While much scholarship in postcolonial studies has affirmed that the symbolic value of the vernacular liberates the colonized psyche for national or anticolonial struggle, my dissertation compares the aspirational rhetoric and performative gestures of vernacular projects with responses to vernacular language use. Furthermore, the project analyzes the ways vernacular language projects responded to emergent political forms and the disappointments that often accompanied them, as with the West Indies Federation’s failure in 1962 and the political ruptures within Haiti following diaspora and the departure of the dictator Jean-Claude Duvalier. I begin with George Lamming’s figurative anticolonial conversation in The Pleasures of Exile, moving to the readerships of Haitian writer Frankétienne’s literary efforts to resist dictatorship through novels in Haitian Creole and French, to live theater and radio audiences of Caribbean diasporas, finally ending in Caribbean state institutions dedicated to the cultural politics of language. Ultimately, these uses of vernacular language only symbolized the participation of the masses whose speech was invoked while power remained with an ever-shifting elite.