To extend the insightful points articulated by Di Bianca and Mahalik (2022), I bring into focus the landmark contributions of Carol Gilligan whose large body of scholarship (1982, 1993, 1995Gilligan et al., 1990) on human development in a patriarchal society is largely overlooked in the present article. Gilligan's critique of patriarchy, power, and inequality in science and society pushes us to center the cultural ideological context in this conversation, which extends beyond boys and men and masculinity. Our efforts to promote healthy masculinities must coincide with (re)structuring society to center the margins and dismantle the cultural ideologies that engineer inequality and undermine the core human needs, capacities, and desires of all humans. Cultivating a culture of authentic relationships is not only the key to promoting healthy masculinities but the pathway to nurturing healthy humans and societies.