This book explores how two generations of relatively privileged Australian men have navigated the complex terrain of same-gender friendship across their lives, to offer both empirically unique and theoretically significant insights into the mechanics of social change in masculinities. Applying a feminist poststructuralist lens to data from in-depth interviews with 14 pairs of fathers and sons, it details how masculinist discourses of emotion and intimacy have governed the participants’ friendship practices at three chronological timepoints: fathers’ early lives and later lives, and sons’ early lives. A clear but complicated shift emerges, such that the commitment to stoicism and self-reliance dominant in the fathers’ early lives has given way to a growing embrace of intimacy and emotional expression within their and their sons contemporary same-gender friendships. Engaging with key debates in the field of critical studies on men and masculinities (CSMM), this book offers an alternative to the conceptualisation of this positive change as either representative of a holistic disintegration of hegemonic structures, or a superficial behavioural shift that is largely inconsequential to the gender order. Rather, it illustrates that the increasing influence of feminist, queer-inclusion and therapeutic discourse has destabilised masculinism in the context of men friendships, offering men an alternative subject position that allows care, expressiveness and intimacy. This book will be of interest to scholars in Gender and Sexuality Studies, and Masculinity Studies.