The patient that presents with oral and facial pain can prove a diagnostic conundrum. Whilst most often dental causes can explain the origin and help from our maxillofacial colleagues is warranted, it is useful to have a system for approaching facial pain. This review details how the underlying trigeminal system is responsible for nociception in the head and neck region. There is then a detailed overview on history and exam with a particularly useful section on intraoral examination and dental assessment, as well as neurological and vascular examination to identify less obvious causes of pain, and in addition a section on red flag symptoms. The schema detailed for psychosocial evaluation is helpful in providing a holistic approach to diagnosis. Finally, readers are recommended to familiarise themselves with the International Classification of Headache Disorders III (Beta Version) for a standardised classification of facial pain disorders. This is a useful article for all ENT specialists to help approach a common outpatient condition.