Psychotherapy with the Borderline patient consists of a complex ongoing series of mutual conscious and unconscious interactions. Both the therapist and the patient act and react countertransferentially and transferentially to their own and each other's issues. When these complex interactions are unconscious and not understood by the therapist, they cannot be consciously explored in the realm of a mutual therapeutic endeavor. This article focuses on a number of characterological countertransference issues which either impede or become detrimental to the psychotherapeutic outcome. Recommendations are made regarding enabling therapists to more effectively address these issues.