We examined how the experience of high-quality listening (attentive, empathic, and nonjudgmental) impacts speakers’ basic psychological needs and state self-esteem when discussing the difficult topic of a prejudiced attitude. Specifically, we hypothesized that when speakers discuss a prejudiced attitude with high-quality listeners, they experience higher autonomy, relatedness, and self-esteem than speakers who share their prejudiced attitude while experiencing moderate listening. We predicted that autonomy need satisfaction would mediate the effect of listening on speakers’ self-esteem even when relatedness, a well-documented predictor of self-esteem, is controlled for in mediation models. Two experiments that manipulated listening through in-person interactions with high-quality or moderate listeners supported these hypotheses. Theoretical and practical implications are discussed, with a focus on the role of experiencing high-quality listening for speakers’ state self-esteem during difficult conversations.