Together with the diary and dramatic monologue, Augusta Webster’s poem “A Castaway” achieves a fiercely critical appraisal of Victorian society and the subjugation of its female community. Provoking the performativity of the monologue, the diary enables and empowers the voice of the protagonist, affording a space—A Room of One’s Own—to sincerely and persuasively relay the societal injustices that pervade the life of the Victorian sex worker and that thrust them into the darker, morally depraved recesses of Victorian society. The novelty of this paper is its investigation of the purpose of the diary as it relates to dramatic monologue and the interrogation of identity. Simply put, this paper argues that the diary—as surrogate auditor and instrument of consultation—enables the speakability of the protagonist, and this speakability is demonstrated by the candid outspokenness of the dramatic monologue. This paper’s usage of the term “speakability” connotes the ability to freely voice one’s speech: in this case, the unfiltered criticisms of the speaker and her appraisal of society at large. If we consider Judith Butler’s coinage of the term “impossible speech”—“the ramblings of the asocial, the rantings of the ‘psychotic’”—speech that fails to subscribe to conventional interpretations of accepted speech, then “speakability” can be understood as the uninhibited (arguably unbridled) freedom to speak candidly without the restrictions of speech that the Victorian sex worker was typically consigned to. From the disparity between innocent girlhood and adult courtesan to the symbolic nature of the diary as both a literal and figurative mouthpiece, this paper interrogates the female Victorian’s outlet for communication and consultation.