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