In Taiwan, the necessity and importance of combining the “professional education” and “Life Education” has been promoted in recent years. This article is an action research that shared the experiences and reflections of a teacher educator who infused life education into teacher education by planning and implementing a life education course in a teacher education program. One of the critical theme in the course was to discuss the predicaments in life, that is, the “loss”, “frustration”, and “nothingness” as experienced by both the teacher and her students in their adolescent years. By analyzing various documents including interviews, student assignments, self-reflection notes, this article elucidates the perceived dimensions of life predicaments; the ways with which individuals attempt to face and transform them; and the ways in which teachers may help in guiding their students to face and transform the predicaments. In such a way, this course has created a space for teacher education and pre-service students to meet and to ponder upon life predicaments as a person as well as a teacher.