Generalized essential telangiectasia was well defined more than 30 years ago. There have been no reported cases of associated gastrointestinal (GI) bleeding. Recurrent hemorrhage in the setting of telangiectases, including GI bleeding, is more typically associated with hereditary hemorrhagic telangiectasia. We report a unique case of a woman with generalized essential telangiectasia and GI bleeding from a watermelon stomach. We include a brief review of the literature of watermelon stomach, generalized essential telangiectasia, and hereditary hemorrhagic telangiectasia.