Empathy is originally raised by humanistic psychology, and gradually it has been adopted by psychologists of many other Ḁelds, including psychoanalytic psychology dynamic orientation. Empathetic listening is an important aspect of empathy, especially to the Teenagers. Many worldwide researches have already demonstrated that rigorous education (emotional abuse) brings bad effects to children and teenagers. The famous concepts, “good-enough-mother”, “holding environment”, and “facilitating environment”, raised by D. W. Winnicott, is beneficial to make a family a good start-point in the life-long road, and empathy works well and do make improvements in family education. This article extracts a dialogue from the popular novel Bad Kids to show how to operate empathy in family education.