Imperforate hymen is a genital outflow abnormality that can occur in females. It can present with various symptoms and is associated with short- and long-term complications that may affect patients’ quality of life. Acute urinary retention in adolescents is a rare occurrence. We report a case of delayed diagnosis of imperforate hymen involving multiple visits to the clinic for urinary symptoms and the subsequent development of acute urinary retention. Awareness of this rare presentation is essential since delayed diagnosis is associated with hydronephrosis, endometriosis and infertility in later life.