In psychoanalytic work the analyst is confronted with an ongoing dialectical tension between two gender-related states. One is the fact that each member of the dyad is nominally male or female. The other is a state of gender fluidity involving multiple contradictory gender identifications as well as moments in the process that are not infused with any specific gender experience. In this communication we look at this tension from the standpoint of gender-based stereotypes, developmental issues involving differentiation, foreclosure-disavowal, and countertransference struggles with the identifications thrust upon the analyst by the patient. Both “in synch” and “out of synch” identifications may be repudiated and disavowed in different clinical situations.