Trichobezoars are concretions of retained, undigested material, mostly hair or hair-like fibers in the stomach. Rapunzel syndrome is the condition when trichobezoars extend into the small bowel, leading to various complications including bowel obstruction, and perforation due to pressure necrosis. We present an interesting case of trichobezoar in a 15-year-old female patient, who presented with abdominal pain for one month duration. The exam was notable for a firm palpable mass in the epigastric area associated with localized tenderness and guarding. Contrast-enhanced CT of the abdomen showed a distended stomach with the bezoar, dilated duodenal loops, and clumping of proximal jejunal loops. Upper gastrointestinal endoscopy showed a trichobezoar extending from the oesophagogastric junction to the pylorus. Endoscopic removal of the trichobezoar was not successful.  An elective laparotomy was performed, during which the stomach, duodenum, and proximal jejunum were dilated. The trichobezoar, measuring 35 cm in length, extended from the body of the stomach to the proximal jejunum and caused jejunal perforation due to pressure necrosis. The trichobezoar was removed and primary closure of jejunal perforation with diversion gastrojejunostomy and jejunostomy was done. There were no postoperative complications. The patient followed up with psychiatry in the clinic after discharge, she was diagnosed with trichotillomania and started on fluoxetine, with improvement in her behavioral symptoms. In young female patients with nonspecific chronic abdomen pain and a palpable mass, trichobezoar should be considered in the differential diagnosis. Contrast-enhanced abdomen CT is the preferred imaging modality and removal of the trichobezoar with an appropriate endoscopic or surgical procedure is the treatment of choice. It is essential to diagnose and treat the underlying behavioral condition to prevent recurrent episodes.