Adolescence can be best summarized as a time of authenticity, passion, and advocacy. As adolescents start maturing, on a life journey that leads them away from dependence on their parents to becoming an independent adult, they often seek out honest and transparent mentors to learn from and trust for wisdom and guidance. Although Thomas Merton, the celebrated spiritual author and Cistercian monk, is better remembered for his writings on ecumenism, nonviolence, and advocacy, he also had several documented correspondences with adolescents throughout his life. By examining these artifacts, it is clear that Thomas Merton had great insight into the spiritual needs and challenges of adolescents. Throughout his life, Merton’s authentic struggles often parallel the searching nature that defines adolescent spirituality. Through scholarship and practice this book will explore how the life and writings of Thomas Merton may serve as a guide and bridge for ministers of adolescents, and will offer some practical suggestions for minsters, educators, and parents on topics affecting contemporary adolescents, through the lens of Thomas Merton’s life and writings.