A number of psychosocial factors have been associated with the onset, exacerbation and/or maintenance of chronic pain in adolescents. The present study was conducted to evaluate the relative importance of vulnerability, reinforcement, and modeling. We compared 222 adolescents with chronic pain and no documented physiological etiology (headache, back, limb and abdominal pain) with 148 controls and their (respectively 183 vs. 127) parents. Analyses showed that adolescents with chronic pain are more vulnerable in terms of neuroticism, negative fear of failure, and (less) experienced social acceptance. Contrary to our expectations, the chronic pain group experienced less reinforcement for their pain behavior by both parents and peers than the control group. While the number of pain models was higher in the chronic pain group, no differences were found between their parents and those of the adolescents without chronic pain in pain experience, pain parameters, and pain coping. Regression analyses on the contribution of psychosocial factors to chronic pain and its parameters sustained the positive relation between vulnerability, (less) pain reinforcement, pain models and coping with pain. Furthermore, we also found evidence that gender differences have to be taken into account.