Although transgender individuals have been part of every culture and society in recorded human history, many people today are unaware of gender variant individuals among them and discussions of rights and equality have usually excluded trans people. This lack of recognition and intolerance often makes being transgender today very difficult. Much work remains to be done to educate the public and improve the safety and well-being of trans people. College professors can help to promote understanding of and advocacy for gender variant individuals. This is an overview of one professor’s experiences in weaving critical thinking and dialoguing about the transgender experience into two very different college courses through documentaries and/or literature.