This article examines how the constructions of gender, female sexuality, nation, and war by the Organization of Ukrainian Nationalists and the Ukrainian Insurgent Army influenced their attitudes to intimate fraternization between women (both members of the nationalist underground and civilians) and enemy men between 1939 and the mid-1950s. Conclusions are based on the analysis of a wide range of sources. The article highlights various forms and methods of repressive measures against women who transgressed sexual norms. The article argues that the violent practices against women were not standardized, and largely depended on subjective decisions of the local leaders and commanders, as well as on the level of women’s engagement in the underground activities. Violence against women represented a tool of preservation of patriarchal power and traditional gender roles but became one of the means of constructing power relations among the nationalist men, as well as their relations with enemy men.