A 15-year-old girl was admitted to the Pediatric Emergency Department due to abdominal discomfort, anorexia, diarrhea, emesis, and weight loss. An inflammatory bowel disease diagnosis was suspected and a complete endoscopic investigation was deemed necessary. Initially, only colonoscopy with ileoscopy was performed, with evidence of widespread ileal ulcers, whereas a subsequent esophagogastroduodenoscopy revealed a huge trichobezoar that was further surgically removed. Trichobezoars are intraluminal conglomerates composed of ingested hair and are typically associated with underlying psychiatric disorders. Bezoars can be asymptomatic or present with various gastrointestinal symptoms, mimicking, among other conditions, inflammatory bowel disease. They may extend through the pylorus into the jejunum leading to Rapunzel Syndrome, which may cause intestinal obstruction. The treatment of trichobezoar depends on its location and volume. An endoscopic approach is possible for small-sized trichobezoars, but to avoid bezoar tail migration along the intestine, causing obstruction, conventional laparotomy is the only valid treatment for patients with Rapunzel Syndrome. Due to the increasing incidence of psychiatric disorders in pediatric age during the SARS-CoV-2 pandemic and their relationship with trichobezoars, an increase in cases of trichobezoars was observed. Thus, interdisciplinary collaboration between psychiatrists, pediatricians, and surgeons is crucial not only during the acute phase but also for long-term management and prevention of recurrence.