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Reported rates of sexually transmitted infections (STIs) among midlife Canadians have increased. However, there is little data on the STI behavioural risk of this age group. The current study investigated the prevalence and correlates of condom use at last penile vaginal intercourse (PVI) among sexually active single (never married, separated/divorced) Canadians aged 40 to 59 (n = 830). Men were more likely than women to report using a condom at last PVI (35.3% vs. 27.6%). Number of partners, dating status, partner type at last sex, and concern about STI were significant bivariate predictors of condom use among men and women. Age, marital status, and erectile difficulties were additional bivariate predictors for men. In multivariate analysis, marital status, number of partners, and partner type predicted condom among men. Divorced and separated men were 53% less likely to use a condom than single, never married men. Men who reported 2 or more partners over the past year were almost 2 times more likely to use a condom than men who had one partner over the past year. As partner type at last sex moved from casual to more committed, men were 26% less likely to report condom use at last PVI. Among women, partner type at last sex was the only significant multivariate predictor of condom use, as partner type moved from casual to more committed, condom use was 33% less likely. Condom use was not associated with decreased pleasure during PVI. Educational STI prevention interventions targeting single midlife Canadians are needed.