This article aims to study the representations of gender and, particularly, “masculinity” in the poetry of the nineteenth-century Portuguese author António Nobre. In it, I use a theoretical approach that is rarely used to study Lusophone literatures and Lusophone poetry, in particular: gender studies and masculinity studies with references to sociological and anthropological models that study the construction of masculinity. The article’s argument is anchored in an oft-quoted sentence once uttered by the poet Teixeira de Pascoaes when asked whether he admired the poetry of António Nobre. Pascoaes famously said: “Of course I like him, he is our greatest poetess!” Besides constituting a provocation, the sentence provides glimpses into the sexual codes of behavior (and of poetic production) that were prevalent in Portugal during the nineteenth and the first half of the twentieth century. Among other things, these codes define the kinds of poetry that a man should and should not write. By looking into the social (and sociological) implications and assumptions behind Pascoaes’s provocative sentence—against the background of António Nobre’s own sexually subversive poetry—I hope to shed light both on the gendered nature of Portuguese normative poetics during the times of António Nobre and Teixeira de Pascoaes; and on the way António Nobre subverts these genderic mandates in his poetry.