In the USA, as many as 1 in 6 women nationwide become adolescent mothers, making adolescent pregnancy and childbearing issues a frequently encountered occurrence by pediatricians and adolescent medicine health care providers. Both social and medical programs focus on prevention and management of adolescent pregnancies; however, caring for the adolescent-headed family is less well understood. For many teen parents, various environmental and behavioral risks contributed to early childbearing and parenting. Following delivery of the infant, many of these same psycho-social, environmental, and educational factors continue to play a role in the teen's ability to parent effectively. This review explores these factors in relation to teen parenting as well as describes the limited data available on outcomes of adolescent mothers and their infants. Despite negative social stereotypes regarding adolescent fathers, research suggesting that most fathers desire involvement with their infants and the impact of and factors influencing father involvement is explored. Understanding the dynamics of the coparenting relationship, an expanding field of study, will aid practitioners in strengthening and supporting teen parenting by both mothers and fathers. As most teen parents continue to reside with their families, teen parenting has an important impact on the multi-generational family structure. These relationships can serve both to support and at times to hinder the adolescent parents' development as an individual and as a parent. Successful interventions and programs to support the adolescent-headed family take on various forms but are usually comprehensive and multidisciplinary and consider the developmental status of both the parent and the child. To best care for adolescent-headed families, pediatricians and adolescent medicine providers should understand the psychosocial, developmental, educational, and relationship issues that influence adolescent parenting.