This autoethnographic needs analysis uses the sociopolitical framework of precarity (Travers, 2018) to contextualize the researcher's experience of learning and teaching languages as a transgender man—first as a student undergoing gender transition, and then, later, as a transgender assistant English teacher in Japan. These needs are shown to have been opaque, ambiguous, and prone to change over time, indicating the significant challenge of identifying and meeting needs of LGBTQ+ students while addressing issues related to gendered language in the classroom. Because of the potential pitfalls of teaching political topics in the classroom (Byram et al., 2021), taking a perspective of intercultural exchange and awareness-raising is recommended, with the goal of developing learner awareness of potential communication challenges related to gender identity and expression. The analysis concludes with specific suggestions, such as grammatical and pragmatic instruction in the use of singular "they" (Grote, 2020), using realia such as SNS accounts to raise awareness of changing pronoun conventions in English, and the pros and cons of strategies such as "pronoun signposting" in the creation of a gender-friendly classroom environment (Airton, 2019).