The potential impact of cumulative inequality upon loneliness in later life is under-researched. This study applies Ferraro and Shippee’s axioms of cumulative inequality to the narratives of two Northern Irish older women, who completed semi-structured diary entries over a 16-week period, recording and reflecting on their social lives and their personal histories. The two women were subsequently interviewed on the basis of what they had recorded. These stories reveal how the life trajectories of these two individuals are influenced by the different experiential impact of bonding and bridging social capital. Despite similar life experiences, significant and substantial differences emerged in the women’s stories, relating to work life, social class, the restrictions of a caring role, and physical and mental health. These two narratives not only provide evidence of the impact of cumulative inequality on loneliness but also highlight the lifetime impact of socio-economic status and access to capital affecting older women’s vulnerability to loneliness.