Transference-countertransference involvement with patients the analyst finds “pleasurable” is examined. Analysis of such patients courts the danger that pathological identifications will go unrecognized and the analysis end at a point where the opportunity for decisive change, which to the patient appears physically and psychically catastrophic, is forgone. A presentation of one aspect of the analysis of a young woman reveals the psychic pain experienced by analysand and analyst when the feared breakdown places a pathological identification in doubt, and the difficulties that can ensue in treatment. Other psychodynamic lines of interpretation and differential diagnostic considerations are put aside in favor of an examination of the special role of enactment and countertransference enactment and their impact in promoting development or strengthening defense.