Changes in political, social, and economic structures in South Africa during the transition from apartheid to democratic governance in 1994 have put men and masculinity/ies under public and scholarly scrutiny. Attention has generally focused on the links between masculinity and violence, particularly among black men from low-income backgrounds, in attempts to understand the widespread levels of sexual violence throughout the country. Together, but in tension with the focus on men and violence, has been a literature that documents gender change in South Africa. This literature argues for example, that men are embracing fatherhood and becoming more engaged in childcare. Nevertheless this is a minority literature that is overshadowed by a focus on men and violence. In this article, I reflect on the lives of a group of men living in Alexandra township in Johannesburg, who are exploring what it means to be a man in a contemporary township setting, and the issues and challenges they face in attempts to transition their masculine identities.