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In 1923, the Portuguese writer, pedagogue, and feminist activist Ana de Castro Osório, travelled throughout Brazil to deliver a series of lectures, published in Lisbon in 1924 as The Grand Alliance. This paper explores how her eponymous São Paulo lecture articulated and enacted modes of conviviality as she promoted her titular vision of a grand alliance between Portugal and its former colony. She emphasized the two nations’ ‘mutual worth, dignity, and essential similarity’ – in Gilroy’s words – to advocate strengthening Luso-Brazilian cultural ties at a time when many Brazilian writers and artists were engaged in a defiant cultural nationalism. However, she rooted this sense of ‘essential similarity’ in the ‘grand’ racial heritage of the Portuguese and their Brazilian ‘children’, and prophesied their shared cultural supremacy. My paper also addresses this potential dark side of similarity as a basis for conviviality.