The prevalence of obesity in the United States is projected to increase as high as 85% by 2030. Weight loss is associated with improved morbidity and mortality outcomes. Roux-en-Y gastric bypass (RYGB) is an effective procedure recommended for individuals with morbid obesity for weight loss. We report the case of a patient who developed worsening food allergic reactions after RYGB surgery that progressed to an anaphylactic reaction. A 36-year-old female developed an anaphylactic reaction to an ingredient in guacamole eight years after RYGB surgery. Prior to the surgery, she had symptoms consistent with oral allergy syndrome. After the gastric bypass, however, she experienced worsening symptoms. On this occasion, she developed throat tightness prompting a visit to the emergency department where she required emergent intubation for airway protection. Blood testing to assess for an immunoglobin E-mediated allergy to common foods was negative. Despite the negative test, the allergist maintained a high suspicion for the progression of food-pollen syndrome following gastric bypass. Disruption of protein digestion from stomach bypass surgery may result in dietary proteins large enough to elicit immune responses being presented to the immune-rich intestinal mucosa. Additional consideration should be given to patients with a preexisting history of food allergic reactions undergoing RGYB surgery.