In this commentary on Tara Babiak's analytic work with a very disturbed, almost autistic young man, I take up the function of gender categories as defense and as potential; the power of enactments in analytic treatment; and the difficulties of homophobia in patient, analyst and culture. I focus on the uses and functions of gender and ideals of masculinity in the patient's identity. A central enactment early in the treatment gave rise to intense transference and countertransference scrutiny. I suggest the long shadow cast by this enactment, which was both hopeful and provocatively destructive. I discuss the quandaries (analytic, personal, and cultural) for the analyst working with a patient for whom phobic dread may be a defense against fragmentation and madness.