This paper utilizes a heuristic arts-based inquiry to explore the author’s countertransference while working as a drama therapist with an LGBTQ group living with internalized homophobia. The paper contains a literature synthesis spanning topics of internalized homophobia, psychotherapy and creative arts therapies with LGBTQI individuals as well as the methodology used by the author to understand his experience of the working with the said group as a drama therapist. The heuristic methodology provides a framework and a context for the arts process in accomplishing the aims of the above inquiry. The research process will be informed by the Moustakas model of heuristic research, which includes the six steps in heuristic methodology. The last step of this research involves a film presentation that captures the author’s experience and ends with some reflections on the process.