In 1868, Louis May Alcott crafted an engaging post-Civil War story in Little Women, a tale of four adventurous young women crossing implicit and explicit borders as they mature into adulthood. As they dream and act out their lives, they cross-dress, cross oceans, cross gendered work boundaries, confound domestic expectations, and even cross one another as loyalty and love are tested. But, let's face it. Although a heart-warming novel for the ages, Little Women is quaint. Why, in 2005, the era of Toddlers and Tiaras and Mean Girls, did producers, writers and performers invest time, money, and energy into adapting this quaint story into a Broadway musical? In this paper, I assert that the answer must lie in the creators' pursuit of an imagined audience. Specifically, this inquiry explores librettist Mindy Dickstein's adaptation process of Alcott's Little Women, with a focus on the textual, musical, and production choices aimed at appealing to a twenty-first century American female audience members. While there have been many adaptations of the Alcott material (including stage productions, films, British television series, Japanese anime, and web series), the 2005 musical Little Women offers a lens to examine the impact the commercial Broadway apparatus can have on the choices involved in the adaptation process and casting the star persona. Featuring primary interviews with Dickstein, this paper highlights the subtle changes that illuminate the ways in which this production and its star performance reflect the changes in American women's (both young and old) place in society and in the manner of their representation through the reciprocal relationships of text, audience, and cultural context.