A discussion on Chandigarh Kare Aashiqui (Chandigarh does romance, 2021), a recent Bollywood film starring Ayushmann Khurrana, who begins a sexual relationship with a woman unaware that she is transgender. The film has generated controversy for its casting of a cis-gender actress (Vaani Kapoor) to play the role of the trans character. This discussion explores how such a casting choice paradoxically allows for a critique of transphobia to emerge, allowing audiences to question their prior assumptions regarding gender and gender identity. These are themes that are seldom explored in mainstream Bollywood, making this film’s engagement with the topic all the more salient today.