Psychological well-being (PWB) is crucial for personal and societal growth, revolving around an individual’s mental state and life satisfaction (Ryff & Keyes, 1995). Fulfilling close relationships is believed to significantly impact PWB by fostering emotional regulation and self-worth (Tan, 2020). Therefore, this study explores the association between fulfilling close relationships and psychological well-being by examining the duration of conversation and frequency of smiles during interactions. Employing a naturalistic observational design, sixty participants were observed at the University of Maryland’s Yahentimitsi Dining Hall. As predicted, the results showed a significant positive correlation between conversation duration and smile frequency. Since this was an observational study, there was high external validity and minimal participant reactivity. However, limitations such as the difficulty in operationalizing close relationships to be accurately measured and the limited ability to control potential confounding variables, such as participant’s mood, in the observational design. Understanding that close relationships significantly contribute to psychological well-being suggests the importance of investing in initiatives aimed at strengthening social connections. Programs such as mentorships, community-based activities, and support groups can provide platforms for individuals to cultivate and sustain fulfilling relationships. By prioritizing strategies that facilitate social integration, policymakers and stakeholders can enhance individuals’ overall quality of life and promote mental health on a societal level.