Bernard Shaw emerged as a public figure and strident social commentator in the 1890s, a period when public discourse was largely dominated by topics that generally coalesced under the umbrella of ‘The Woman Question’, and were often signified by the iconic figure of the New Woman. Sarah Grand, a foundational figure in ‘New Woman’ writing, nonetheless believed ‘this Gorgon’ to be more a journalistic fiction than a reality. Reforms to the Married Women's Property Act (1870, 1882), the availability of certain educational and career opportunities to women, the increasing prominence of a counter-discourse condemning a gendered double standard, and agitation for female suffrage were all helping to foster a new sense of independence and self-determination for women – and a concomitant sense of anxiety in society at large. Luckily for Shaw, the egalitarian goals and reformist zeal of this first-wave feminism resonated strongly with his own socialist ideals. Shaw's alliance with many of these feminist campaigns gave him access to some very publicly visible platforms, allowing him to establish himself as a progressive thinker and social critic, although his sometimes more equivocal attitudes to feminist goals – and individual feminists – meant that Shaw was perhaps not always quite as useful for feminism as feminism was for Shaw.

The ‘New Woman’ was educated, physically fit, rationally dressed, and independently minded. She smoked, sought career opportunities, and demanded an end to a gendered double standard. She was enough of a contradiction to the ‘ideal’ Victorian woman that she ‘furnished Punch and the Pall Mall Gazette with both a target for attack and a way to release anxiety about changes in the Victorian social order’. She was also a target for attack among conservative (male) writers, including dramatists like Sidney Grundy, whose play The New Woman (1894) was a popular success. Like Grundy, Shaw first invoked the New Woman on stage to undermine her. Julia Craven (The Philanderer) and Gloria Clandon (You Never Can Tell) are New Women who are easily outsmarted by their male suitors precisely because of their advanced views and education.