The writing of the Medieval period has been influential for centuries yet is often simplified by caricatures of the brave knight and lovely damsel. Especially in terms of gender, this period in western history is particularly strict and binary. However, through unique authors such as Marie de France, a rare female writer of the period, we can see complex, yet subtle, presentations of difference that may be unexpected to some readers. Within the lays of Marie de France, I aim to analyze the feminized male figures of Lanval, Guigemar and Bisclavret as models of gender difference using a lens of modern gender theory, specifically the ideas of theorists such as Judith Butler and R.W. Connell. These male figures of demonstrate deviations from the standard medieval masculinity through androgyny and hyper-masculinity in ways unique for the period. The conventions of the Western medieval culture are then subverted by the supernatural, making the lays lasting examples of gender expression. Using modern theory, we can take a step back from previous historical periods and try to better understand the society and culture of that time and place. By examining these male figures of difference and medieval standards of masculinity of a context long past we can see how to grow and progress further in the modern day. Gender can be understood as a social construct even centuries ago, exemplified by the unique figures of difference presented by such authors as Marie de France. Keeping that in mind, we can reanalyze literature in innovative ways and continue to seek new understandings of gender and masculinity.