When the author's patient Sam first came out as trans, both analyst and patient assumed he would benefit from switching from an ostensibly cisgender psychoanalyst like the author to someone transgender, like him. In the end, Sam decided to stay with the analyst, all while transitioning from female to trans male and then giving birth to his biological offspring. The analysis profoundly affected the analyst to such an extent that she can no longer even casually refer to herself as merely “cisgender” without adding quotations around the term and the qualifier “ostensibly.” As someone assigned female at birth, the analyst might not have expected to need to make such stipulations. Whereas initially, the analyst could only see Sam's possible gains from a potential switch to a trans analyst, she later realized that something might also have been lost. When Sam decided to stay with the analyst, she worried about being a supportive and good enough “trans-parental” object for him but later realized how the psychoanalytic process could be endangered by the wrong kind of “transpositive” attitude. In this article, the author explores the concept of cisgender, asking about the ways in which queer theory and dialectical psychoanalysis can constructively inform each other, and the ways in which the author's own “queering” experience contributed significantly to the clinical process.