Hematometrocolpos is a rare congenital abnormality of the female urogenital system that leads to an imperforate hymen and subsequent retrograde menstruation. We present the case of a 14-year-old female patient who presented to the emergency department with amenorrhea and abdominal pain, and was found to have an imperforate hymen and hematometrocolpos on trans-abdominal point-of-care ultrasound. It is important for emergency physicians to consider this diagnosis in pubescent female patients presenting with abdominal pain, as missed diagnosis can lead to infertility and other complications.