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This article describes some dilemmas in the analysis of a man with perverse traits and various manifestations of anxiety who displayed an intense idealizing sexual transference. The phenomenon of sexualization is analyzed in terms of its possible genesis, as well as the affects it is intended to defend against by their magical transformation. This sexualization is linked to the body's pain and excitement, seen as the tension between its surface and its depths, which often cannot be symbolized. Issues of truth and falsity, honesty and duplicity, and the location and relocation of the disavowal-generating split inherent to perversion are addressed as well. Another issue in this analysis, closely linked to the countertransference, is the need for and danger in saying “no” to the analysand's assaultive sexuality and the handling of the paradoxical blend of his idealization and his naive, defensive, defenseless lack of comprehension of “why not” (have sex, make love, become a couple). “Why not?” is regarded by the author as a seminal question concerning perversion, both in its constitution and in questions of technique associated with it.