In the context of feminist and postmodern thought, traditional conceptions of masculinity and what it means to be a “Real Man” have been critiqued. In Genevieve Lloyd's The Man of Reason, this critique takes the form of exposing the effect that the distinctive masculinity of the “man of reason” has had on the history of philosophy. One major feature of the masculine-feminine dichotomy will emerge as a key notion for understanding the rest of the paper: the dichotomy of reason-feeling, a parallel and a foundational aspect to the dichotomy of masculinity and femininity. In exploring the history of symbolic conceptions of masculinity in ancient Greece, the Renaissance, and the present, one finds that the oppression of women is integrally linked to the traditional tie between masculinity and reason. There have been many efforts in recent feminist philosophy to rewrite or redefine “Woman” in such a way as to alleviate the oppression of women. I argue that the effectiveness of rewriting Woman for this purpose is problematic, primarily because any rewriting of this type must occur in the current historical context of hierarchical dualisms, like Man-Woman, masculine-feminine, male-female. These binary oppositions arguably find their roots in Pythagorean philosophy and can be traced through the Renaissance to our current historical context. It is these dualisms that have traditionally valued the masculine side of the Man-Woman dichotomy more than the feminine. Further, it will be argued that the hierarchical dualism of Man and Woman is so pervasive that if we rewrite or redefine the inferior, deprivileged side of that dualism, we cannot correct its devalued status. Instead, we redefine that which is undervalued but retain its devalued status. This particular aspect of attempts to critique hierarchical dualisms like reason and feeling has been reflected in the writings of many feminists, male and female. This paper will show that in cases where women attempt to redefine the dichotomy by revaluing the traditionally feminine (like feelings and emotions) over the traditionally masculine (like reason) their work is often mistakenly criticized for being purely political; conversely, when men attempt to redefine the same dichotomy in an attempt to allow men to “get back in touch with their feelings,” to be nurturers, their work is described in terms of providing a better epistemology. The current literature on masculinity explores alternatives to rewriting or redefining Woman that try to avoid the problem of status remaining with redefinition. This alternative is rewriting or redefining Man. Through redefining Man, one may be able to reconceptualize the privileged side of the hierarchical dualism in such a way that it is no longer privileged. Deprivileging, as well as redefining Man, is argued by theorists of masculinity to be possible because while the devalued status of the inferior side of a hierarchical dualism tends to keep the same status when redefined, it may be possible to redefine the privileged side of the dualism in such a way that it loses its privileged status. Unfortunately, many of these attempts to rewrite or redefine masculinity have detrimental faults of their own. Finally, this paper will discuss more promising possibilities for new definitions of Man, as well as a vision for better interaction between the work of women and men in general.