AbstractDoes fear of being single (FOBS) predict risky health behaviors when such behavior could promote pursuit of a romantic connection? Study 1 tested general tendencies toward taking health risks associated with FOBS. Study 2 tested how those with stronger FOBS navigated romantic versus non‐romantic risk behavior during the COVID‐19 pandemic. Study 3 extended the test of risky behavior beyond the pandemic to test whether FOBS was associated with willingness to engage in risky sexual behavior. Despite nonsignificant associations with taking health risks more generally, FOBS was associated with greater willingness to engage in risky behaviors in dating contexts, particularly when considering their willingness to settle for less in relationships. This research provides novel insight into dating choices associated with stronger FOBS and how willingness to settle predicts risky health behavior when it could appeal to romantic prospects.