Little is known about what it is like to age as a gay man. This study explores the psychosocial well-being of older gay men, including associations between present life experiences and self-esteem and subjective well-being. A nationwide community-based online survey was conducted involving 840 Australian gay men. Results showed men aged 60 and over were poorer and more likely to live alone than those in their 40s and 50s but drew greater support from friendships and community organizations. Although less optimistic about their future, they had higher self-esteem and rated their subjective well-being no lower than their middle-aged counterparts. Good physical health, a satisfying sex life, feeling supported, and fewer experiences of discrimination were key factors in self-esteem and subjective well-being. These and other findings offer important insights into the psychosocial well-being of older gay men that health and social support services ought to consider when working with this population.