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This paper examines life-long singlehood and its ramifications in old age among women and men in Ireland. During the life-time of the 26 research participants, Ireland shifted from the Western European marriage pattern, characterised by high rates of singlehood, late marriage and high fertility, to declining prevalence of singlehood, higher marriage rates and lower fertility. In-depth interviews were analysed with the help of narrative analysis and grounded theory methods. We identified two main pathways into singlehood that had a long-term impact on the participants' lives. The women and men who had chosen singlehood associated this status with independence, self-fulfilment and autonomy throughout their lifecourse, including in old age. In contrast, older adults who had been constrained in their choice of marital status due to poverty, care work, family roles and cultural norms, expressed regret and dissatisfaction with their single status. In the latter group, the ramifications of the inability to actualise the roles of a spouse, parent and grandparent were particularly apposite in later life when many felt the absence of close ties and expressed loneliness. For some of the older adults who had been constrained in their choice of marital status in earlier life, the possibility of entering into a romantic relationship seemed more feasible in later life. How older adults interpret their pathway into the single status in earlier life impacts on relationship formation and life satisfaction in older age. [ABSTRACT FROM PUBLISHER]