During his time of service in the Italian Army in World War I, Ernest Hemingway was injured. He received a non-life-threatening wound and was forever changed. In his article, "Ernest Hemingway: The Life as Fiction and the Fiction as Life," Jackson J. Benson proposes the idea of Hemingway's "wounding what if?" that follows this course of thought: "What if I were wounded and made crazy?, what would happen if I were sent back to the front? I was only wounded in an accident, what do the really brave ones think of me? (351)" Shortly following the war, Hemingway was wounded a second time, this of an emotional nature. A British nurse whom he had fallen in love with broke his heart by downplaying the relationship they had shared and his emotions for her. These two young experiences seem to have impacted Hemingway's writing a great deal, leading him to color his wounded male characters as feminized. "From Wounded to Woman" is an exploration of a variety of Hemingway's wounded male characters that attempts a connection between their having incurred these wounds and becoming feminizied. There is a direct line of logic-of-assertion followed from Hemingway's most popular character, Jake Barnes, through to some of his lesser-known short story stars that traces a path of consistent wounding and subsequent feminization. In the more narrow literary world, Ernest Hemingway has been known as a masculine author whose tales are of war and suffering. It is my goal to explore the feminine aspects of Hemingway's work through his self-critiques expressed through his leading male characters.