The implications of the global trend of declining fertility rates and an increasingly ageing population have been extensively reported. Childless men are, compared to women, missing from gerontological, psychological, reproduction, and sociological research. These fields have mainly focussed on family formation and practices with the fertility intentions, history, and experience of older men being overlooked. Over the past 15 years, research literature on both involuntary childlessness and ageing has highlighted the paucity of material on men’s experience. Infertility research has shown that failure to fulfil the status of parenthood may lead to a complex form of bereavement and is a significant challenge to identity. In the past three decades, there has been an escalation in the research and general literature surrounding fathers, fathering and fatherhood. Recent research into contemporary grandparenting has highlighted the intricacy and importance of intergenerational relationships to grandfathers. Drawing on my auto/biographical PhD study, this piece examines how 14 self-defined involuntarily childless men managed non-fatherhood. The findings demonstrated the complex intersections between the men’s attitude to childlessness, fatherhood, and non-fatherhood across the life course. The actions and attitudes of the men as they negotiated the movement from pre-transitional to a post-transitional stance towards fatherhood, demonstrated the different strategies each adapted in order to negotiate their procreative remit. This study countered the stereotype that fatherhood is not important to men and challenges research that reports that men are not affected by the social, emotional, and relational aspects of involuntary childlessness.