Given new developments in the field of adolescent reproductive health, this review focuses on highlighting new guidelines and practice patterns in evaluation and management of adolescent gynecologic problems. First, understanding the proper techniques for the initial examination is key to establishing a long-term relationship with this age group. Reservations about the first gynecologic examination are common, and the practitioner’s goal is foremost to make the patient as comfortable as possible. Preventive health in this patient population is key, and practitioners should become comfortable with providing education about topics as diverse as sexuality, eating disorders, and dating violence. Furthermore, the frequency with which teenagers report sexual activity and the high unintended pregnancy rate in this age group makes counseling regarding effective contraception essential. Additionally, practitioners are encouraged to take the opportunity to discuss the availability of the human papillomavirus (HPV) vaccine with adolescents. In 2007, adolescents were designated as a special population, given the frequency with which they acquire and clear mild HPV-related cervical dysplasia. More conservative treatment in this population is generally favored. During their transition through puberty, disorders of menstruation become the most common complaint requiring the attention of the gynecologist. Most commonly, anovulation serves as the cause behind such abnormal bleeding. Polycystic ovarian syndrome can develop in early puberty and carry its consequences into adulthood. Infertility, diabetes, and hirsutism mark the most important components of the syndrome and require age-appropriate management. Finally, the consequences of endometriosis on the future fertility of adolescents have brought early intervention to light. Recognition and prompt treatment are advocated to prevent the future implications of this disease.