Understanding MSM’s decision to indulge in unprotected anal intercourse (bareback sex) in relation to his awareness of HIV/AIDS risk is essential to develop effective HIV/AIDS prevention programs in Davao City. This study used decisional balance to bareback (DBB) scale in computing the net difference scores between bareback and condom use. Thus, the decision of an MSM to bareback could be interpreted in association between DBB and awareness to HIV risks. A diverse sample of men who bareback (n=40) was recruited through Respondent Driven Sampling (RDS). RDS was used to statistically adjust for the biases inherent in how persons of similar characteristics are networked and likely to recruit each. Exploratory factor analysis was used to explore the domains within the DBB scale, and test the association using Kendall tau correlation between DBB and HIV/AIDS risks awareness. Two underlying factors in the DBB scale, found to be moderately true for them: a Coping with Social Vulnerabilities subscale (Sex with condoms makes me feel better about myself; x=4.32) and a Psychosocial Vulnerabilities subscale (Sex with condoms helps me feel less depressed; x= 4.00). Although the findings showed that MSM had a higher level of awareness in HIV/AIDS risks, results showed no significant association between DBB (i.e. greater gains associated with bareback sex) and awareness in HIV/AIDS risks. MSM are a high-risk group for HIV infection in the southeastern part of the Philippines, Davao City, making it 2nd in rank in terms of the highest incidence of HIV positive persons in the whole country.