This conversation, commemorating twenty-five years of the Journal of Women's History, was convened as a joint project of the Coordinating Council for Women in History (CCWH) and MARHO: the Radical Historian's Organization. Preparation for the panel discussion began with an email exchange among some of the participants. Iris Berger and Judy Tzu-Chun Wu were unable to participate in the panel discussion at the American Historical Association (AHA) conference in 2012, but their email comments are included here, as are other contributions from the preliminary conversation. The AHA panel in Chicago brought together major senior and junior scholars whose work encompasses both radical and women's history to address the intersections of the two fields. All of the participants were asked to consider questions including: How did the origins of the fields connect? How have their trajectories converged or diverged across time? What have been the crucial developments in radical history, in women's history, and in radical women's history? What might the future hold for radical women's history?