This case highlights vague abdominal pain in an adolescent female and its various differential diagnoses. In uncovering the ultimate diagnosis of hematometrocolpos, three clinical pearls are imperative to highlight that make it worthy of further discussion among pediatric emergency medicine and emergency medicine providers. First is the importance of a thorough genitourinary exam in pubescent females, a component of the physical exam that is often deferred for a multitude of reasons, as was in this patient. Discussion of this prompts training programs in emergency medicine to emphasize the importance of uncomfortable components of physician skills, such as the uncommonly practiced pelvic exam. Second is the consideration of uncommon diagnoses when vague complaints do not respond to standard therapies or fit common diagnostic criteria in a particular age group. Lastly, physicians should take advantage of the timely and effective use of bedside point-of-care ultrasound, which has the ability to make diagnoses efficiently and therefore reduce time to life-saving management. Altogether, while its low incidence makes it challenging to diagnose hematometrocolpos routinely, emergency medicine physicians must remain astute in suspecting the diagnosis. Overlooking it may lead to severe consequences such as perforation, endometriosis, adhesions, fallopian tube damage, and infertility.