This study reports on one-on-one interviews and focus groups with gay and bisexual men over forty, concerning their vulnerability to HIV. Respondents report a range of age-related issues that impact on safer sex decision-making including decreased attractiveness, widowerhood, loss of support networks from AIDS, and anticipated future quality of life, as well as strengths and satisfactions that decrease their risk. Respondents typically attributed unsafe sex in other men to popular discourses around (1) condom fatigue, (2) treatment optimism, and (3) inserter invulnerability, but deny that these ideas explain their own behaviour. They identify their own risk situations with: depression, impending mortality, trading off safe sex, and the effect of condoms in keeping erections. Community-building projects that begin to address risk situations have followed from this research with the AIDS Committee of Toronto.