The aim of this paper is to explore the links between the attachment-theory derived concept of disorganized attachment, and the psychiatric diagnosis of Borderline Personality Disorder (BPD). Disorganized attachment can be understood in terms of an approach-avoidance dilemma for infants for whom stressed or traumatized/traumatizing caregivers are simultaneously a source of threat and a secure base. Interpersonal relationships in BPD including those with care givers is similarly seen in terms of approach-avoidance dilemmas, which manifests themselves in disturbed transference/countertransference interactions between therapists and BPD sufferers. Possible ways of handling these phenomena are suggested, based on notion of 'meta-cognitive monitoring', in the hope of re-instating meaning and more stable self-structures, in these patients' lives.