While transgender representation in media has improved in quantity over the last decade, the representation of transgender men in video games is still limited. In this work, I examine the character Tyler from the game Tell Me Why as a critical case study toward the representational adequacy of transgender people in video games. Through a focus on character design, narrative, paratexts, and game reception, I explore the ways Tyler is a more complex example of transgender representation. Additionally, I argue that the act of bringing transgender people into character creation results in a more complex representation.