Anita Loos’ novel, Gentlemen Prefer Blondes, first appeared in a 1925 issue of Harper’s Bazar to commercial success. Often compared to F. Scott Fitzgerald’s The Great Gatsby, as both depict the 1920s and were published the same year, Blondes, the novel, and Loos herself would fade into relative obscurity. What little scholarship there is reads Lorelei within a binary of “dumb blonde/gold digger. This perpetuates the patriarchal, sentimental binary construction of female characters (and women) which limits them. I aim to challenge that understanding through my work revealing that the dumb blonde/gold digger are both sentimental categories, and Lorelei’s own “Professional Lady” is something else entirely. Lorelei works to explode the categories and redefine what it means to be female. Her “Professional Lady” positioning is one that is more powerful, more knowing, and more linguistically in control of writing herself as a woman who knows the game and wins.