In March 2020, in response to the COVID‐19 pandemic, Canadian provincial governments instituted a variety of public health measures that included social distancing and isolation, which may have had unintended consequeses. According to the Loneliness and Sexual Risk Model, gay, bisexual, and other men who have sex with men (GBM) often cope with loneliness through risky sexual behaviors. Previous studies have demonstrated that COVID‐19 measures such as social distancing and isolation led to increases in loneliness; thus, these measures may also have led to elevated sexual risk‐taking among some GBM. Participants were recruited from an ongoing cohort study on GBM health and well‐being, and were included in the current analysis if they had completed relevant study questions (n = 1134). GBM who reported lower levels of social support pre‐COVID‐19, were younger, and lived alone each reported greater loneliness during the first year of COVID‐19. Although feelings of loneliness did not predict sexual risk‐taking within the first year of COVID‐19, loneliness did predict greater sexual risk‐taking 6 months later. Additionally, younger GBM and those living alone were more likely to engage in sexual risk‐taking at both COVID‐19 data collection points. These findings offer some support of the Loneliness and Sexual Risk Model; however, it is possible that the unique circumstances of the COVID‐19 pandemic resulted in a temporary suspension of this association, as many GBM took steps to protect themselves and partners in the context of COVID‐19.