Aims: Patients with different facial pain/headache pathologies usually complain of numerous accompanying symptoms relative to systemic dysfunctions or to the patient's personality characteristics. The purpose of this work was: (1) to determine the prevalence of accompanying symptoms in groups of patients with temporomandibular joint (TMJ) dysfunction and other types of facial pain or headache disorders, (2) to assess the patients' personality characteristics and anxiety levels, and (3) to see whether significant differences were found between the groups. Methods: Two hundred forty-three patients were considered. They had TMJ intracapsular disorder (TMJ, n = 71), tension-type headache (TH, n = 52), migraine (M, n = 68), chronic daily headache (CDH, n = 26), or facial pain disorder as somatoform disorder (FP, n = 26). The presence of 23 symptoms was assessed; the Minnesota Multiphasic Personality Inventory (MMPI) and the Spielberger State and Trait Anxiety Inventory (STAI) were administered and the relative scores were calculated. Four different MMPI clusters (depressive, conversive, emotional, coper) were also considered. Intergroup differences were assessed by Chi-square analysis, 1-way analysis of variance, Bonferroni t test, and a logistic regression model and then standardized for gender and age, taking the tension-type headache group as a common reference group. Results: The TMJ group had: (1) a lower prevalence of almost all symptoms; (2) significantly lower scores of several MMPI and of state anxiety; and (3) odds ratio values 1 for all symptoms except phobias and for emotional, conversive, and depressive MMPI profiles. The FP and CDH groups had the highest prevalence of the majority of symptoms and higher MMPI and STAI scale elevations. Conclusion: It is concluded that some types of headache and facial pain seem to correlate with the presence of a number of accompanying symptoms and with some changes in personality. These changes are particularly relevant in patients with chronic daily headache and facial pain disorder. In contrast, patients with TMJ intracapsular disorders tended to show a low prevalence of accompanying symptoms and a normal personality profile.