My chapter presents an intertextual comparison of early eighteenth-century letters to the editor (LTEs) published in English and Colonial American periodicals on the topic of women’s roles and their relationship with men, as experienced—or constructed as being experienced—by both male and female correspondents. By presenting LTEs as a space for civic engagement, my analysis focuses on the forms of evaluation and intertextuality in the correspondents’ personal narratives and general reflections. My aim is to identify discursive similarities and differences in how English and Colonial American readers represent, discuss, and problematise the man-woman relationship within a patriarchal system, while attempting to promote happiness at both personal and societal levels. To this purpose, I examine: (1) explicit and implicit forms of evaluation and how they contribute to reinforcing or challenging the male-dominant ideology across the Atlantic; (2) forms of intertextuality within the text-type and between English and American LTEs. While English correspondents favour the familiar letter style, emphasising personal grievances that ultimately reinforce the male-dominant ideology, American correspondents tend to prefer essays in letter form, where a marked normative order coexists with female attempts to challenge male prejudices and carve out a discursive space for the redefinition of their role.