Since the 1990s, there has been a growing realisation that gender polarisation does not promote girls' and women’s interests. Although critics, especially radical feminists or womanists, have argued that this trend is diluting women’s struggles, there are benefits to be gained from girls and women working with boys and men. While there are different, often competing forms of masculinities, it is important to identify and work together with progressive masculinities for positive transformation. This chapter discusses the theme in honour of Ezra Chitando, with particular reference to how his academic work has influenced his family’s pathways. Contrary to the past, where family settings were generally the bastions of patriarchy and male privilege, there are progressive men who have questioned old patriarchal traditions. They believe in social justice and transformation. Such men transform, challenge and confront cultural beliefs and practices that stifle social justice and oppress girls and women. They are willing to construct new and alternative masculinities based on equality. This chapter is an appreciation of the distinguished work of the feminist, Ezra Chitando, and an acknowledgement that girls and women need to strategically build alliances with progressive boys and men in order to ensure sustained
social transformation.