In contemporary times, the conceptualisation of marriage has shifted; however, societal attitudes and cultural ideologies regarding its construction remain complex. As such, unique generational perspectives are needed to reflect on how marriage has evolved and to comment on ongoing tensions related to it. This study explores how individuals born in the 1960s conceptualise marriage, examining the complex interplay between traditional values and evolving perspectives. Using an exploratory qualitative design underpinned by a social constructionist epistemology, semi-structured interviews were conducted with 12 participants (7 female, 5 male) aged 56–65. Reflexive thematic analysis revealed three main themes: (1) Unveiling the New Vows: The Shifting Values of Marriage and Family, (2) Breaking Boundaries and Transforming Traditions: Debunking Heteronormativity, and (3) Witnessing Progression: Dismantling Barriers and Embracing Diversity and Equality in Marriage. The findings indicate a significant shift in how marriage is viewed, with participants demonstrating both nostalgia for traditional constructs and support for more inclusive definitions. Notably, many participants positioned themselves as more progressive than their peers, challenging notions of homogenous generational attitudes. This study highlights the ongoing tension between traditional and contemporary views of marriage, suggesting that efforts to promote inclusivity must address both legal barriers and deeply ingrained cultural norms. These findings contribute to our understanding of how social institutions like marriage are reconceptualised over time, emphasising the dynamic nature of social change and the capacity for individuals to evolve in their perspectives on deeply entrenched societal norms.