Based on ethnographic material from northern and central Namibia, this article provides insight into the views and experiences of primarily unemployed and poor men, and the dilemmas with which they are confronted due to lack of life opportunities. For these men, poverty and lack of agency may lead to loss of meaning and identity. The article brings men's experiences into context by exploring the socio-economic and historical transitions which in powerful ways contribute to shaping men's lives. It argues that HIV/AIDS is but one of many pressing concerns, and therefore information campaigns to promote safe sexual practices have limited meaning and impact. It further argues that men, like women, but in different ways than women, are vulnerable to HIV/AIDS. To counter this situation, it is crucial that HIV/AIDS prevention efforts work with men specifically. If prevention programmes are to have any relevance and impact, they should take their starting point in men's experiences of social exclusion and existential doubt.