This book tells a story of masculinity through the experiences of one boy, 'Adam'. From four different studies and time periods, it tracks moments of significance in his life over a period of 20 years. These moments highlight the ways in which Adam is both drawn towards and away from a hegemonic masculinity of physical toughness, domination, competition and an opposition to 'the feminine'. The book is set against the backdrop of a long history of contentious gender politics in Australia and globally but particularly responds to the renewed attention to the social construction of masculinities in the current #MeToo climate. Against this backdrop, nuanced and longitudinal accounts of boys' and men's experiences of masculinity are significant because they can offer insight into the complex bodily, social, economic, and historical forces that configure masculinities. Such understandings are important in our endeavours as those who educate, support and work with boys and men to transformgender inequalities.