Interrelations between the circulation of images concerning race and gender in the context of global hierarchies and new local forms and meanings of partnership and prostitution in Cuba have not been adequately understood until now. This is due to the image of a “sudden” revival of prostitution, after it had allegedly been eradicated in socialist Cuba. Exploring prostitution, marriage and womanhood in Havana from a historical perspective and examining jineterismo as part of the local ‘informal’ economy, this article demonstrates how these institutions were modified in a global context long before the 1990s. In the transcultural relations between foreigners and locals, models of womanhood, partnership and love were not merely ‘given’ by the social structure in the context of a globalized modernity. Instead they were to a large extent influenced by ideas concerning gender, race and morality, created and negotiated by agents as they interacted, Cuban women having resorted to these ideas and related institutions as arenas of empowerment.