This study proposes a transactional model for the reciprocal relationship between increased likelihood of adolescent sexual intercourse and decreased connection with the perceived environment. Connection with the perceived environment is operationalized as higher problem-focused interactions with parents, lower religious attendance, and lower school belonging. Relationship with the perceived environment is further hypothesized to explain the increase in depressive symptoms associated with initiating sexual intercourse in adolescence. Data from Waves 1 and 2 of the National Longitudinal Survey of Adolescent Health (one year apart; valid N=10,873) were analyzed using survey-adjusted multiple and logistic regression and path analysis. Hypothesized relationships were confirmed, with an additional finding that relationships with the perceived environment do not improve with the cessation of sexual intercourse. Implications of a possible explanation for this, that this finding indicates sexually active youth earn a stigmatized "non-virgin" label that they cannot easily remove, are discussed.