Decades of research have focused on the importance of social connection for overall functioning and well-being. However, very little work has explored social connection as experienced during conversations, as opposed to globally or with particular partners. Because social connection is a property that emerges out of individual conversations, creating a tool to measure connection felt during specific conversations is vital to further the understanding of social connection. Across the three studies described in Chapter 2, I validated the CDCS in a sample of nearly 1,000 adults. Results revealed that each subscale was uniquely related to various positive well-being outcomes. Specifically, the Shared Reality subscale was uniquely associated with conscientiousness; the Affective Experience subscale was uniquely associated with autonomy and loneliness; and the Partner Responsiveness subscale was uniquely associated with life satisfaction and positive affect in the last seven days. In an experimental study described in Chapter 3, I validated an adolescent version of the CDCS in a sample of 4,055 adolescents who reported on nearly 6,500 face-to-face and digital conversations combined. Results revealed that adolescents rated conversations that took place over video chat as more connecting than conversations that took place face-to-face, over social media, or over text. When examining the well-being and health outcomes of connection felt during face-to-face and digital conversations, very few differences emerged. However, when comparing the strength of the effect of connection felt during face-to-face and digital conversations, connection felt during face-to-face conversations had a more uniquely powerful influence on positive well-being and health outcomes, such as fewer headaches and more life satisfaction, compared to digital conversations. Taken together, my two dissertation studies demonstrate the importance of measuring social connection not just globally or for a specific partner, but also at the conversation level. The CDCS is a valuable tool for future researchers to understand social connection felt in specific conversations both face-to-face and digitally. Future research should continue to explore the connection felt in face-to-face and digital conversations, including how individual conversations may aggregate and strengthen over time to positively impact global connection, well-being, and health.