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While countertransference in its various definitions has become central to psychoanalytic theory and practice, and countertransference is acknowledged as central to most care-giving practices, the opportunities to know and explore countertransference in most mental health training programs is limited. Applying approaches of Narrative Medicine didactics, this paper proposes and demonstrates how the group study of clinically relevant literature (novels and short stories) under guided discussion can lead to the identification and exploration of countertransference reactions. The scope of this paper is to report on a single class taught for ten years using literature to teach adolescent development with the finding that it became a forum to explore various countertransference arising in psychotherapies with adolescents, an approach that can be broadly applied.