Using archival materials, court documents, contemporary scientific research, and newspaper articles, my work analyses the cultural meaning of widespread haircuttings perpetrated by a figure known as ‘Jack the Clipper’ against young, white women in Boston, Chicago, and New York between 1888 and 1910 to reveal the mechanisms by which a new infrastructure of (hetero)sexual desire was formed. Rather than understanding heterosexual desire to be an innate or unified attribute that finds different social and cultural expression, my work uses these violent encounters with Jack the Clipper as ways of examining the changing and conflicting direction(s) of sexual desire at the turn of the century. Building upon interrogations of the ‘orientation’ in sexual orientation from queer and spatial theorists, I re-frame the emergence of heterosexuality as a spatial transformation that leveraged the formidable social, physical, political, and economic disorientations of the 1890s to narrow appropriate sites of desire by enacting violence against urban-dwelling women, and bring into alignment sexual desire, new constructions of whiteness, and the form of the American city. Chapter 1 introduces the narratives of the women who were attacked by a clipper, implicating haircutting as a form of sexual violence and mechanism of gender oppression and arguing that bodies were re-oriented from constellations to locations of sexuality through sexual violence. Chapter 2 examines hair as a sexual fetish, using the emerging language of sexology to reveal the process of re-orienting sexual objects and object choices. Chapter 3 reveals the reorientations of white identity vis-a-vis Blackness that minimised the (white) violence of Jack the Clipper and left the cultural space of the mythic Black Rapist unchallenged. Chapter 4 argues that the refusal of police departments and courts to acknowledge the transgressive behaviours of clippers prompted communities to police clippers on their own, revealing the tensions between popular sexual beliefs and sexual norms advocated by middle-class proponents of the American state. Finally, chapter 5 theorises large-scale spatial dis-orientation in American cities as newspapers and train networks annihilated time, space, and scale, creating a form of ‘spatial nausea’ that re-shaped the cultural infrastructure reproducing heterosexual orientations.