In this paper the author, a Taiwanese American cis-gender mother and clinical psychologist, presents some observations from her personal experiences of parenting her transgender nonbinary teenager, as well as observations from her experiences working with another cis-gender Chinese American mother who sought parental guidance with her transgender nonbinary teenager. The author describes how her own parental experiences opened greater appreciation for the multiplicity of responses in the processes of parental reflective functioning and integration that can come up for parents, as they improvise in the task of parenting across gender difference. The societal contexts of racialization of Asian American parents, judgments of parents’ transhomophobia, discrimination against LGBTQ+ youth, and mental health are also discussed.