This paper explores whether postmodern gender theory can fully account for how a “cis” gender (gender and biology match) therapist works with a “trans” gender patient in a relational way. Inspiring contemporary queer theory exists courtesy of experts in the field, but how does a nongender expert deal with the complicated enactments that occur when patient transitions her gender from female to male and then decides to become pregnant? It is suggested that this case may more accurately represent an example of a post-postmodern analysis, in that it holds the dialectic of constructed gender within the realities of a social system that remains deeply gender binaried.