Social connection is an important aspect of well-being and health, yet there is confusion about its definition and development. Study 1 examines common conceptualizations of social connection, namely quantity and closeness of relationships, and loneliness to determine how they interact to form a larger social connection construct. Data from 125 participants were analyzed using structural equation modelling (SEM), the results of which indicated that loneliness and relationship closeness best comprise the model. Study 2 replicated these findings with a larger, independent sample (N = 159), and examined a model of the possible development of social connection using Brown’s (2010a, 2012) notion that increased self-compassion, authenticity, and vulnerability lead to improved social connection. Parental (in)validation of negative emotions was added to provide developmental context. Results indicated that the concepts proposed by Brown relate to one’s level of social connection. Specifically, the data were consistent with the possibility that recalled parental emotional invalidation leads to decreased self-compassion, and increased ambivalence over emotional expression. Individuals with increased ambivalence over emotional expression, in turn, reported lower levels of authenticity, which may lead to less adaptive social connection, defined as closeness in relationships and loneliness. Overall, these findings have implications for the childhood development of emotional expression, and the far-reaching effects of parenting.