This study examined the hindering and helpful events that transgender and gender-nonconforming Ontarians experienced in therapy. To explore descriptive accounts of these experiences, we employed a systematic and rigorous investigation using the significant events framework and thematic analysis to interpret findings. Eleven participants underwent semi-structured interviews, providing rich accounts of their recent therapy experiences alongside their contexts and impacts. From these interview transcripts, we constructed eight major themes relevant to the research question: (1) Helpful and Hindering Relational Gestures; (2) Expectations about the Therapist’s Role; (3) Therapist’s Perception of Transness; (4) Topics in Therapy; (5) Significant Relational-Emotional Experiences; (6) Significant Event Impacts on the Client; (7) Client Processes in Understanding Significant Therapy Events; and (8) Contexts. Implications for therapeutic work are discussed.