In Canada, progress towards reconciliation with Aboriginal Peoples has been slow, in part because of a lack of emphasis on interpersonal reconciliation—changes in the beliefs, attitudes, and behaviours of non-Aboriginal Canadians. Physical distance, prejudicial public discourses, and insufficient, ineffective education for the public pose barriers to renewed relationships between settlers and Aboriginal Peoples. Drawing from transformative learning theory and pedagogy for the privileged, this narrative inquiry examines critical events in the lives of eight white settlers living in Mi’kmaw territory in Nova Scotia. The study uncovers factors which have prompted some Euro-Canadians to take up their responsibility for reconciliation and enabled them to stand as allies with the Mi’kmaq. The transformation process in settler allies was catalyzed by a combination of personal, intrinsic, and extrinsic events. New relationships between settlers and the Mi’kmaq were founded around shared interests or goals, and friendships provided an important foundation for learning. Hearing the personal stories of Mi’kmaw people challenged stereotypes and misinformation about Aboriginal Peoples. Settlers’ learning was further supported by immersion in Mi’kmaw communities or contexts, time spent on the land, and mentoring by Mi’kmaw people. Allies reported that the satisfaction they derived from relationships with Mi’kmaw people as well as a desire to do good and see justice done sustained these relationships over the longer term. The study suggests that a lengthy period of awareness raising and confidence building followed by opportunities for informal, experiential learning and face-to-face interactions are key elements in settler decolonization.