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While Little Women (1880) has garnered serious critical attention, scholars have consistently framed Louisa May Alcott’s An Old-Fashioned Girl (1870) as a minor work. In problematizing previous feminist approaches to Alcott’s oeuvre, this essay casts an analytical gaze toward marginalized males within the text, and explores how Polly Milton’s maternal power overshadows a selection of male characters in Alcott’s novel. Specifically, I argue that Mr. Sydney (as a genteel aristocrat) and Tom Shaw (as a contemptible boy) represent culturally marginalized masculinities, at odds within discourses of (male) exceptionalism and the self-made man at large across industrializing nineteenth-century North America. In discussing these specific male characters’ inconsequential masculinities, as read alongside Alcott’s presentation of Polly as an empowered female character, I reformulate Eve Kosofsky Sedgwick’s theory of the triangular relationship, expressed in Between Men, in which a woman is exchanged between males as a kind of property. By presenting Polly’s outright rejection of a female role, I speculate that Alcott twists gender inequalities. Reading Alcott’s characters as an inversion of Sedgwick’s triangulation, this paper asserts that it is the female character, Polly, who takes advantage of males (Mr. Sydney and Tom). These are marginalized masculinities who become invisible while Polly is presented as both powerful and, therein, highly visible.