First bite syndrome (FBS) is a sharp unilateral pain in the vicinity of the angle of the mandible after taking the first bite of a meal that presents typically after surgery in the area of the ipsilateral parapharyngeal space. It is not confirmed what the pathophysiology is that causes this pain, but the proposed mechanism is the iatrogenic damage of sympathetic fibers that extend from the superior cervical ganglion (SCG) to innervate the parotid gland. The presentation of this syndrome has been acknowledged in patients who have undergone head and neck tumor resections, but it has not been documented in the same thorough manner among vascular surgery cases in the parapharyngeal space, possibly because of a higher risk of development in other head and neck surgeries, or to under-reporting of cases. To date, only 5 cases of FBS status post carotid endarterectomy have been documented in the literature. Definitive treatment of FBS has not been established. Some studies have shown improvement with amitriptyline, and carbamazepine as well as botulinum toxin injections. We will present the case of a 75 year old male who developed first bite syndrome after a right carotid endarterectomy with efforts of raising awareness of a potential acute complication of carotid endarterectomy.