Using archival resources on the data assembled in making the first edition of the OED, as well relevant revisions introduced across later editions, this chapter examines the representation of gender across a period of conspicuous ideological, lexical, and semantic shift. Focussing on the ‘Woman Question’, a topic which, across the late nineteenth and early twentieth centuries, encompassed a range of key issues in gender terms (such as education, political representation, and equality), it explores the cross-currents of dominant ideologies, definition, editorial omissions, and acts of reading as they come to affect the making of the Dictionary. As for newly introduced forms such as the new woman or suffragette, the same terms can be strikingly polysemous, depending on one’s point of view. Lexicographers, as Murray had stressed in his ‘General Explanations’, have, however, ‘to draw the line somewhere’. The chapter explores the difficulty of that ‘line’, as well as the ways in which it can drawn (and redrawn) by different editors across the Dictionary’s history.