The therapeutic relationship has been a cornerstone of the theory and practice of psychotherapy since it first emerged as a healing modality. Research has extensively reported on the therapeutic relationship and its role in the outcomes of psychotherapy. Despite the vast research on the therapeutic relationship, little qualitative exploration has focused on both patient and therapist lived experience. Using a hermeneutic phenomenological qualitative methodology, this study examined the lived experiences of both patients and therapists, within the same therapeutic relationship in a South African context. Three patients and three therapists (i.e. 3 patient-therapist dyads) were interviewed using in-depth semi-structured individual interviews (six interviews in total) to explore their experience of the relationship they developed during therapy, and the meanings that have been made of this. Through thematic analysis, using interpretation to deepen the analysis, several themes and subthemes were identified. Both patients’ and therapists’ lived experiences of the therapeutic relationship in psychodynamic psychotherapy clustered around three major and somewhat similar themes, with various sub-themes. Patients’ lived experiences of the therapeutic relationship centred around the following themes and sub-themes: therapist’s therapeutic approach (holding the patient in mind—knowing them; non-judgmental stance; providing an objective presence— perspective; and a consistent presence), facilitating therapeutic factors (mutuality; and therapist self-disclosure), and process within the relationship (describing the relationship—a lifeline; moment of meeting; change; and the relationship over time). Whilst therapist-participants’ experiences of the therapeutic relationship held somewhat similar themes with subtle differences, namely, patient qualities, facilitating therapeutic factors (holding and containing; theoretical orientation; use of technique; and supportive factors for therapists), and process within the relationship (describing the relationship—intimate yet formal; moment of meeting; change; and the relationship over time). Similarities and differences between patient and therapist experiences are examined that may influence the therapeutic relationship. Conclusions are discussed with a consideration of the limitations of the study as well as implications for future research, practice, and training.