Headache patients demonstrate excessive personality dysfunction, the headache often manifesting the patient's interpersonal stress. Personality disorders result from environmental factors that adversely impact personality, including major single traumas, chronic traumas such as deprivation, neglect, abuse, and abandonment, and child-rearing patterns such as invalidation, communication double binds, and excessive or erratic discipline. Modern approaches to working with the personality of the headache patient are increasingly directed towards trait-based systems of understanding. Alexithymia, somatization, neuroticism, and neurochemical sensitivities are characteristics of headache patients with personality dysfunction that distort the treatment of physical symptoms and make medical interactions more difficult. A careful evaluation of core personality traits, defenses, patient fears, role and attachment patterns, transference-counter-transference feelings, and narrative style of the headache complaint can help the physician develop a thoughtful picture of the patient. This type of evaluation will suggest those modes of medical interaction demonstrated to improve outcome.