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The COVID-19 pandemic brought the world to a halt limiting all interpersonal social interactions. However, it was unreasonable to expect complete social isolation for an undetermined period. More than ever, digital platforms provided a social lifeline, particularly for single individuals. In this paper, we use a subsample of individuals who used online dating platforms during the early phase of the pandemic and had ensuing in-person dates to examine the association of sexual health behaviors pre-pandemic and health behaviors during the pandemic. The research question guiding this study is, does adherence to public health recommendations regarding sexual health pre-pandemic predict compliance to pandemic-related health protocols? Results suggest that pre-pandemic behavior regarding sexual health, primarily condom use, has a significant association with adherence to public health recommendations related to the pandemic emergency. Our results suggest that engaging in behaviors like masking, planning outdoor activities, and avoiding physical contact are constitutive of longstanding patterns of health behavior, particularly in terms of safe sex. Those who claimed engaging in safe sex practices before the pandemic were significantly more likely to engage in protective practices while dating during the pandemic. Besides the politicization of the COVID-19 pandemic and how that influenced behavior, our analysis suggests that once again, the best predictor of future behavior is past behavior.