The social context surrounding chronic pain is important. This is particularly true in adolescent chronic pain, where caregivers can be a key influence on adolescent social and physical activities. To date, research has generally indicated that greater adolescent difficulties are related to greater caregiver difficulties, and vice versa; however, the strength of this relation has not been consistent across studies. Further, it is possible that adolescent and caregiver behaviors are related in a complex and multivariate manner, which may require more complex evaluations of both direct and indirect relations. The present analyses represent an initial attempt at explicating more precisely how adolescent and caregiver behaviors in response to pain influence adolescent functioning. First, a theoretical model was derived and included adolescent social and physical functioning, caregiver pain management behaviors, as well as adolescent and caregiver psychosocial responses to pain. The model was first evaluated with Pearson correlations and then with structural equation modelling using data from 120 adolescent-caregiver dyads. After adequate fit with the data was achieved, caregiver variables were only indirectly related to adolescent functioning via adolescent psychosocial responses to pain. This indirect relation may explain previous inconsistency across studies. Perhaps more importantly, the model tested may allow for an improved understanding with regard to the complex relations among adolescents and caregivers factors. Finally, the need to adequately understand caregiver experiences in response to adolescent pain is highlighted and calls for appropriate intervention in young people struggling with chronic pain are reinforced within these analyses.