A range of prevention strategies have been considered in an attempt to reduce HIV transmission. The use of continuous antiretrovirals (ARVs) in high-risk HIV-negative individuals (pre-exposure prophylaxis or PrEP) and the short-term use of ARVs following a high-risk exposure (postexposure prophylaxis or PEP) are among these strategies. We report a case of the contemporaneous use of PEP and PrEP in a sexual liaison between two men. In an attempt to reduce the number of new cases of HIV infection, a range of prevention strategies have been advocated. Prior to the availability of ARV therapy, the key prevention measure was condom promotion and modifying sexual behaviour such as partner number reduction within high-risk groups. This was followed by: the introduction of PEP, treating all HIV cases with ARVs to reduce the probability of transmission (treatment as prevention) and in the past few years the use of PrEP. Case-control, observational and randomised clinical trial data exist to support these strategies. We describe what we believe is the first reported use of PrEP and PEP in a sexual liaison between two men in Sydney.