The following paper will examine several therapeutic dilemmas around the issue of professional boundaries and the engagement process between a therapist and a client who come from different ethnic backgrounds and sexual orientation, using a literature review and an extended treatment vignette. The clinical issues will be framed within an intersubjective and feminist paradigm. Rather than providing a resolution, this paper intends to raise several intriguing questions that emerged for this clinician during the treatment and while writing this paper. Particular dilemmas that will be examined are the real relationship versus the therapeutic relationship, the therapist's neutrality versus subjectivity, mutual recognition and agency, and mutuality versus professional boundaries in a feminist treatment paradigm.