The COVID-19 pandemic created high levels of stress that negatively affect mental health and well-being. The stress and coping process is influenced by individual difference factors, such as personality, that impact perceptual processes and emotional reactions. Adult playfulness is a personality characteristic that may lead to better mental and physical health outcomes. We test a theoretical model to determine whether the two factors of perceived stress, perceived self-efficacy (PSE) and perceived helplessness (PH), mediate the relationship among playfulness and coping in adults (N = 694). Scores on the Perceived Stress Scale were high indicating high levels of pandemic-related stress. The SEM model demonstrated direct effects of playfulness on PSE, PH, adaptive, maladaptive, and supportive coping. Both dimensions of perceived stress were partial mediators in the relationship among playfulness and coping outcomes. Findings illustrate the pathways by which adult playfulness can amplify or attenuate the impact of stress perceptions on coping strategies. The importance of building psychological resources such as playfulness to boost adaptive outcomes in stressful situations such as the COVID-19 pandemic is discussed. Supplementary Information The online version contains supplementary material available at 10.1007/s12144-022-02870-0.