Hegemonic / Traditional western masculinity is understood to be predicated through the oppression of women through various forms of misogyny and violence and the suppression, subordination and marginalisation of men, particularly through homophobia, to police deviations from hegemonic ideals. A sample of 13 heterosexual men were recruited, aged between 19 and 56 years, sourced from initiatives involved in challenging problematic western masculinity norms and the unfair societal structures that these norms reinforce. In Study One (Part One), Biographical Narrative Interpretive Methods were employed, producing a Collective Narrative which illustrated the commonalities in the men’s lives and their trajectories to becoming adults and allies. In Study One (Part Two), a Critical Narrative Analysis considered what ideological components may be discernible in the participants’ telling of their narratives. The theories that were considered most representative of the told narratives were (highly prosocial) Hybrid Masculinities and Critical Positive Masculinities, both of which incorporate to differing degrees non-traditional components, conducive to the wellbeing of the individual and those around them. A second complimentary study was conducted involving a smaller sample of returning participants’, who’s texts were found to align most with Critical Positive Masculinities. Semi-Structured interviews and Interpretive Phenomenological Analysis illustrated a cyclical process of meaning making, in which the men’s subscriptions to masculinities were found to be largely performative, motivated by a concern with being perceived of as appealing to potential partners; i.e., heteromasculinities. Counter to this, the men masculinised the practice of critical reflexivity; perceiving self-reflection and accountability as a component of their gender constructs. Ultimately, this research contributes much needed data on non-traditional masculinities and showcases a range of wellbeing-enhancing ideologies and practices for men and boys.