Clinicians across disciplines and practice settings are likely to encounter adolescents who are at risk for a pregnancy. In 2010, 34.2/1000 15–19 year old teens had a live birth in the United States, many more will seek care for a pregnancy scare or options counseling. Teen mothers are also at risk for a second or higher order pregnancy during adolescence. This paper provides clinicians with adolescent-friendly clinical and counseling strategies for pregnancy prevention, pre- and post-pregnancy test counseling, pregnancy-related care, and a review of the developmental challenges encountered by teens in the transition to parenthood. Clinicians are in a better position to approach the developmental, health and mental health needs of adolescents related to pregnancy if they understand and appreciate the obstacles adolescents may face negotiating the health care system. In addition, when clinical services are specially tailored to the needs of the adolescent, fewer opportunities will be lost to prevent unintended pregnancies, assist teens into timely prenatal services, and improve outcomes for their pregnancies and the transition to parenthood.