We use the life course perspective to argue that family transitions like divorce and remarriage are turning points in adolescents' lives and that emotional distress associated with these events are shaped by the circumstances surrounding them. Using the National Longitudinal Study of Adolescent Health (Add Health), we explore how family transitions net of family structure are related to two types of emotional distress, acute depressive symptoms and excessive binge drinking, and whether family context moderates these associations. We find that going through a family transition is related to both outcomes, but only under certain circumstances. As maternal-adolescent emotional distance increases, the probability of severe emotional distress following a family transition increases. In addition, transitioning out of a single mother versus a mother-father household is related to a lower probability of reporting acute depressive symptoms.