Being a parent is hard, particularly parenting adolescents, who need to be given choices and allowed the space to learn how to make choices for themselves, even when those choices result in negative consequences. This essay explores how Steven Sondheim and James Lapine's 1987 musical Into the Woods provides relatable stories of the challenges of being a parent, the challenges of parenting adolescents, and just how messy parents and families can be despite everyone trying their best. The stories of Little Red Riding Hood, Rapunzel, Jack, and Cinderella show us various stages, trajectories, and occasional tragedies of adolescents' emerging autonomy, while the Baker's and the Witch's struggles becoming and being parents encapsulate how disorderly and untidy parenting often is. Pediatricians and clinical bioethicists, who are often in a position to scrutinize the choices of parents and teens, should remember that parents and adolescents are almost always motivated by good intentions and doing the best that they can. Perhaps the best we can do is accompany them on their journey "into the woods."