Background: The pterional approach for craniotomy, one of the most used surgical intervention in neurosurgery, results in a series of postoperative changes that, if they persist, affect the patient’s life, social reintegration, and his/her physical and mental recovery. The aim of the present study was to develop and validate a questionnaire for indicating directly affected masticatory muscles groups and facial nerve branches, in patients undergoing the pterional approach in neurosurgery, so that the recovery therapy can be monitored and personalized. Methods: A self-reporting questionnaire consisting of 18 items (12 for postoperative masticatory status and 6 for facial nerve branches involvement), validated on fifteen patients, following three steps: items development, scale development, and scale evaluation, was prospectively applied twice, at a one-year interval (T0 and T1), with thirty-two patients suffering from vascular or tumoral pathology and surgically treated through a pterional approach. Results: No statistically significant correlation could be found between postoperative outcomes and age or gender. Facial nerve branch involvement could not be correlated with any of the assessed variables. Pathology and time elapsed from surgery were statistically significantly correlated to preauricular pain on the non-operated side (p = 0.008 and p = 0.034, respectively). Time elapsed from surgery was statistically significantly correlated to the ability to chew hard food, pain while yawning, and preauricular pain during back and forward jaw movements and gradual mouth opening. Conclusions: We created and validated a valuable patient-centered questionnaire that can be employed as a tool for postoperative assessment of directly affected masticatory muscles and groups of facial nerve branches.