This research explores the potentialities of psychotherapy for the management of chronic pain. The model used is brief therapy of systemic orientation and the chronic pain managed is primary headaches (namely, migraines and tension-type headaches). In order to produce clinically relevant material, this research is carried out within an alternative research paradigm. The raw data are the audio-recordings of two cases: one with a man suffering from migraines; the other with a woman suffering from chronic tension-type headaches (aggravated by migraine episodes). These were selected from a pool of cases because they illustrate the phenomena under study and both completed a follow-up which confirmed an acceptable headache management outcome. The recordings were transcribed in order to be studied using discourse analysis of social constructionist orientation (DA hereafter). The research questions explored are: How were the headache problems, the therapeutic aims and the resources for managing them constructed during therapy? What did the participants do with these constructions? How was this particular type of talk interaction helpful in changing the way these two people managed their primary headaches? DA reveals that: (1) the headache problems are entangled in many vicious cycles, Catch-22 situations and even double-binds, and that these patterns have the tendency to perpetuate the problems; (2) the meaning of the headaches vary from one patient to the other, being greatly influenced by their personal experiences, family histories and interaction with health professionals; (3) these meanings influence the co-construction of the therapeutic aims, with management (rather than a cure) emerging as a more achievable goal, with additional auxiliary aims also becoming very important; (4) specific interventions for managing the headaches and for achieving the auxiliary aims lead to concrete changes; (5) these changes are sometimes generalized for other situations, and therapy is seen as a useful resource. Thus, this study shows some of the potentialities of brief therapy of systemic orientation to manage primary headaches, producing concrete suggestions that can be applied in clinical work.