This article traces the metaphor of entanglement as it appears in the writings of four nineteenth-century authors who were differently involved with the utopian tradition. The connotations of entanglement range from the sexual and political, encompassing the difficulty of reconciling the competing demands of autonomy and solidarity, to the evolutionary and eugenic. William Morris's comments on Henry David Thoreau's Walden (1854) offer the basis for a comparison of the divergent utopian strategies articulated by Morris and Thoreau, setting up the opposition between spectatorship and entanglement. The sexual connotations of entanglement are on display in Nathaniel Hawthorne's The Blithedale Romance (1852), which, when observed, illuminate the existence of a similar problematic, albeit differently resolved, in Morris's News from Nowhere (1890), recalling Morris's response to Thoreau. Thoreau's utopian strategy of individual withdrawal and secession is at odds with Morris's assertion of the political value of collective social transformation through the agency of social revolution. Thoreauvian traces, however, are clearly detectable in the practice of the Samurai in H. G. Wells's A Modern Utopia (1905), in which the metaphor of entanglement has unmistakably eugenic implications, prompting reassessment of the connection between Morris and Wells, particularly in relation to their differing class politics.