This study employed a mixed-method design to test sex-specific parent-child pain associations. Subjects were 179 chronic pain patients aged 11-19 years (mean = 14.34; 72% female) presenting for treatment at a multidisciplinary, tertiary clinic. Mothers and children completed questionnaires prior to their clinic visit, including measures of children's pain, functioning and psychological characteristics. Mothers also reported on their own pain and psychological functioning. Interviews were conducted with a sub-sample of 34 mothers and children prior to the clinic visit and analyzed using a grounded theory approach. The quantitative data suggest stronger mother-daughter than mother-son pain relationships. The qualitative data suggest that girls' pain and pain-related disability is related to an overly enmeshed mother-daughter relationship and the presence of maternal models of pain, while boys' pain and disability is linked to male pain models and criticism and to maternal worry and solicitousness. Boys and girls appear to have developmentally incongruous levels of autonomy and conformity to maternal expectations. The mixed-method data suggest distinct trajectories through which mother and father involvement may be linked to chronic pain in adolescent boys and girls.