This exploratory study examined the nature of therapeutic conversation between helping professionals and homeless persons as an intervention to optimize health. Meaningful conversation occurred in relationships where there was a sense of connection and the presence of rapport. Emergent facilitators of therapeutic conversation included respectful engagement, casual nature of conversation, alternative settings for therapeutic conversation, effective listening, and establishing trust. Barriers included prejudging homeless persons, fear of punishment and authority, and academic and professional intimidation. Central to the study findings was the acknowledgement of the client's personhood. Acknowledgement of personhood is a critical element in engagement between homeless persons and helping professionals.