The German poet and novelist Charles Bukowski has always been surrounded with controversy throughout his life. However, interestingly, it is his politics of gender representation that mostly triggers feminists and researchers together to condemn him for being misogynist, showcasing a degrading image of female characters in his prose writings. The latter genre is seemingly insufficient to directly accuse Bukowski and his literary works of misogyny. While some of his novels attest to a demeaning yet controversial representation of women, his poetry offers a nuanced version wherein heterogeneous portrayal of women becomes prevalent and therefore allowing the space for readers to encounter poems with an amalgamation of positive representations of women—being independent and intellectual. Because the misogynistic representation in Bukowski’s works is open to various interpretations, rushing into a compilation of hateful judgments concerning the author himself lacks justification and argument. In line with this background, the present paper discusses the limitations of the conclusions drawn with regard to Bukowski’s gender politics, arguing that there is a space in-between worth exploring in his literary works. Through a close reading method of textual analysis, the paper concentrates on selected poems from Bukowski’s collection Love is a Dog from Hell (1977) in order to contrast the positive and negative depiction of women. The paper, in other words, strives to bring into question the extent to which misogyny and ambivalence take roles in Bukowski’s gender representation of the female characters. The analysis undertaken has revealed significant results, in which Bukowski’s poetry comes to expose a more ambivalent and realistic approach towards gender—a reading which is highly needed in order to consider the different perspectives and possible interpretations of an author’s work before limiting it, or the author in person, to a set of stereotypical judgment.