This paper examines the issues surrounding teaching men feminism particularly via the medium of online, distance learning. Increasingly, tertiary institutions in the Caribbean are adopting online learning as the way forward to ensure that its citizens are well equipped to enter the global workforce. There is also a move towards increasing the number of tertiary educated males, who are in the minority in many universities and tertiary level intuitions. By focusing on a lesser known area in the research on gender pedagogy and distance learning, this paper highlights the importance of studying the particular challenges and benefits of teaching men feminist theory. This is mainly achieved through data garnered from a sample of learners themselves, and as such is largely a qualitative paper which taps into the narratives of these men as its major source. The personal experience of the author in the area of coordinating an online distance programme also proves to be an interesting perspective for the work. This is buttressed by literature from the leading researchers and academics in the area of distance learning and feminist theorizing and pedagogy. The paper argues that there are unique challenges and benefits in teaching men feminist theory and highlights the benefits and drawbacks of doing so online. It also suggests ways in which the challenges may be surmounted in order to facilitate an increased number of men who are interested in investing in online education and particularly those with an interest in gender studies. “Despite the long history of men’s involvement in feminism, I’ve learned over the years that telling someone, anyone that I am a feminist is bound to have a startling effect. The responses vary, but they usually involve questions, such as “what do you mean?” often accompanied by some stuttered expressions of doubt about whether it is possible for a man to be a feminist, perhaps whether it is even logically possible…women’s embarrassment seems to centre on how my being a feminist diminishes my manliness, while men seem to think I’m crazy.”