Little sociological attention has been paid to the repartnering of older people after widowhood, and how age, gender and the meanings of marriage influence choices about new cross-gender relationships. This paper reports on in-depth, semi-structured interviews with 25 widows and 26 widowers over the age of 65, widowed for at least two years and who had not remarried. Respondents were asked about their current lifestyle and relationships and whether they had ever considered remarriage. The words ‘selfish’ and ‘freedom’ were often used by the widows when describing their present existence, which was associated with not having to look after someone all the time. Few of the widowers mentioned selfishness and this was more likely to be associated with feelings of anger at the loss of their spouse; none of the men associated widowhood with a sense of freedom. The paper argues that the desire for repartnering after widowhood is gender-specific: widows are more likely to choose to remain without a partner for intrinsic factors: the reluctance to relinquish a new-found freedom; while for widowers, extrinsic factors of older age and poor health are more salient issues in new partnership formation choices and constraints.