Feminist scholars dispute that Tim O`Brien`s "Sweetheart of the Song Tra Bong" either reinforces gender stereotypes or challenges them. Criticism from either side of this debate seems to focus heavily on a discussion of female characters within The Things They Carried: Mary Ann, Martha, Lemon`s sister, the older woman at the reading, and Linda. Nevertheless, both sides of the debate mention masculinity only briefly when exploring O`Brien`s portrayal of women. While most Vietnam War writing reinforces gender stereotypes, effectively functioning as the process of remasculinization that Susan Jeffords describes in The Remasculinization of America, I will argue that "Sweetheart of the Song Tra Bong" is distinct from this writing, consequently challenging stereotypical discourses of masculinity. I will focus on O`Brien`s primary female character, Mary Ann, in relation to the text as a critique of gender binaries and also as a challenge for a variety of other dualisms.