Population aging is an issue of mounting importance throughout the industrialized world. Concerns over labour force shortages have led to policies that prolong working life. Accordingly, present-day workforce participation patterns of older individuals are extensively varied. This study utilized the 2007 General Social Survey to examine factors associated with post-retirement paid work, focusing on the interaction between gender and relationship status, among Canadians aged 50 to 74 who had retired at least once. We find that although being in a relationship is associated with a higher likelihood of post-retirement work for men, the opposite is true for women. Our findings suggest that the gendered association between relationship status and post-retirement work results partly from the gendered associations between relationship status and one’s motivation for learning and community involvement, career orientation, and sense of independence. Gendered meanings of relationship status are thus revealed through analysis of post-retirement work.