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The coronavirus pandemic of 2020 transformed the social environment, as stay-at-home orders, social distancing, and mask mandates defined a “new normal” in the U.S. During periods of social structural change— “unsettled times”—individuals are forced to adapt in all areas of life, including their dating practices. Interviews with 74 unmarried women during the pandemic and its aftermath reveal that when the pandemic disrupted U.S. dating logistics and the cultural beliefs that maintained them, it afforded women a critical perspective and the social space to try out new dating strategies. Through reflection, they raised questions not only about the gendered mechanics of courtship, but also about their actual desire for a relationship, the type of person they wanted to be with, and their expectations for relationships after the pandemic crisis. This paper examines how the pandemic’s unsettling of social institutions created an opportunity for women to reject their passive position in the pre-pandemic courtship process and construct what I call “strategies of empowered action.” Women practiced these strategies as they questioned social expectations, de-centered romance, and reevaluated their desire for marriage and the meaning of family. I argue that women’s new strategies for dating are likely to generate durable changes in the future of marriage and family formation.