The transformation of gender relations was an area early Republican reformers targeted in their efforts to modernize Turkish society. Factors such as urbanization, and increased opportunities for education and employment in the growing cities such as Ankara, the new capital city with an expanding bureaucracy, led to the emergence of new urban spaces and a new set of social relations, including new forms of male-female interaction that replaced or were added to the traditional male-female relations. Working primarily from published and unpublished memoirs and diaries dealing with the 1930s, 1940s and 1950s, this paper presents a portrayal of (largely middle and lower class) male-female social relations in the city, particularly in Ankara, where illicit sexual conduct emerged merely as one aspect of increasing male-female interaction in urban life. While existing scholarship has examined a variety of related topics such as gender and education, feminism, and ideological aspects of the Kemalist vision of modern women (as in the works of scholars such as Elif Ekin Akşit, Yeşim Arat, Ayşe Durakbaşa and Deniz Kandiyoti), this paper considers the social history and actual experiences of changing gender relations in the city as revealed to us in first person narratives. The city offered both new opportunities as well as new challenges to men and women, especially young professionals, for marriage, sex, and sexuality. This paper shows that male-female sociabilities outside of the family covered a wide range of relationships such as purely professional relationships in the work place and at school, companionships as roommates, boarder-landlord relationships, traditional forms of matchmaking practices as well as new forms of dating, and various forms of illicit sexual relations. The paper argues that at least some segments of society benefited from the permissive political and ideological climate promoting the ideal of a modern woman, modern life, and companionate marriage, while other groups (such as women engaged in prostitution and many provincial women) were in practice often either left outside of state-driven liberal social climate or were targets of state control and monitoring.