Trichobezoar is a rare condition almost exclusively seen in young females presenting with non-specific abdominal complaints and a history of psychiatric illness. In most patients, it is confined within the stomach; however, in some severe cases, it extends through the pylorus into the duodenum, jejunum, ileum, or even colon, known as Rapunzel syndrome. Conventional treatment includes laparotomy and psychiatric counseling to prevent relapses. We report the case of an 18-year-old female with no previous history of medical or psychiatric illness who presented with chief complaints of upper abdominal pain, nausea, occasional vomiting for the last six months, and generalized edema for the last three days. On examination, pallor, anasarca, and a palpable abdominal lump were present. On blood investigations, severe malnutrition was seen in the form of severe iron deficiency anemia and severe protein deficiency. Radiological evaluation revealed a large trichobezoar on the CT abdomen and endoscopy, whereas CT venography of the brain, done for persistent headache, showed hyperdense thrombi in the cortical veins. Exploratory laparotomy was done to remove trichobezoar, followed by medical management of malnutrition, cerebral venous thrombosis (CVT) with anticoagulants, and psychiatric counseling for trichobezoar. The association between trichobezoar, malnutrition, and CVT in our case is a further area of research.