Men are primarily responsible for the transmission of HIV because of their participation in risk-taking activities and illicit drug use, while men who have sex men (MSM) are major drivers of the HIV/AIDS epidemic globally. This study the lived experiences of eleven (11) male key informants (KIs) residing in Cebu province, who admit having had sexual encounter with the same sex at least once in their life. Utilizing a Husserlian phenomenology approach, a researcher-made interview guide was used in individually interviewing the KIs with strict to data privacy. The data gathered were interpreted using reflexivity and were using the Colaizzi strategy. The lived experience of MSM, as individuals, presented eight paradoxical themes: belongingness, romantic and sexual relationships, predictability, safety, behaviors on sexual initiation, inclination, identity disclosure, and the circumstances preceding an MSM sexual encounter. This paradox shows how MSM are unique from one another and needs to be simultaneously attached to and separate from the society. Just like any other heterosexual human beings, MSM face various situations in their day-to-day encounter, which may directly or indirectly impact their behaviors and their health. Both government and non- government organizations (NGO) should raise social awareness on the impact of stigma towards MSM population, and promote public knowledge about the motivations, risk-taking behaviors and safety practices adopted by the MSM in response to persistent health threats and sexual prejudice.