HIV/AIDS has had a considerable impact on sub-Saharan Africa and its population for the past several decades yielding a range of consequences on the family as well as on the community as a whole. Malawi is one of the nations in this region that has not seen its HIV/AIDS prevalence rate decrease significantly over the years and is at an estimated 11% (UNAIDS/WHO, 2008). The AIDS epidemic in Malawi has been compounded by other health concerns, economics, education, and social networks which in turn impact prevention and intervention practices and policies. AIDS research has in recent years examined more social and environmental factors in addition to the epidemiological, biological and behavioral aspects. And yet the prevalence rate continues to remain high in Malawi. A review of the literature points to a disparity between knowledge and behavior, frustrating prevention efforts and suggesting that perhaps there is something being overlooked in research and practice. This study utilizes grounded theory methodology in a secondary qualitative analysis, examining 64 in-depth interview transcripts of adolescent men in rural Malawi for any added insight into the disparity between knowledge and associated behavior. Due to the constraints of a secondary qualitative analysis, there were challenges in strictly following the grounded theory methodology. Results of the study yielded themes centered on condom use, gender roles, economics, and education as well as social networks and cultural stigma; these themes were then compared to individualistic, critical, and institutional (or collective) perspectives. Key findings of the study included the disparity between knowledge and associated behavior change reflected in some of the literature as well as a departure from the stereotypical view of gender roles and gender inequality in relationships. Findings also supplemented those key findings from the original data for which the data was collected, providing implications for practice, policy, and further research.