In Singapore, the number of reported Human Immunodeficiency Virus (HIV) cases has increased from 2 in 1985 to a cumulative total of 5,521 as of end June 2012. The current trend in HIV/AIDS is that infected individuals are at a late stage of infection and the majority of the diagnosed HIV infections among men are through heterosexual and homosexual routes. Understanding risky behaviours and the attitudes that sustain it helps identify strategies that can be employed during opportunistic counselling to encourage safer sex and regular voluntary testing. Moreover, beyond promoting condom use which can be challenging for healthcare providers, evidence indicates better understanding of the lifestyle preferences an individual adopts which can lead to targeted interventions for at-risk groups. Changing the message of condom use from protection to good sex and safer sex has resulted in greater condom use in some countries such as Cambodia.