On a June, summer day at Albion College, Byron Stokes and Dudleigh Vernor, two undergraduate members of the local chapter of Sigma Chi fraternity, sat down at the college organ in Dickie Hall and coined the most famous song in fraternity history, "The Sweetheart of Sigma Chi" ("The Sweetheart of Sigma Chi," n.d.a). The tune describes a nostalgic reimagination of a sweetheart who has long since left the arms of the singer and works to conjure up a romantic visualization of a sweetheart through poetic, whimsical lyrics (Vernor 1911). The widespread adoption of the song positioned it as a staple in popular culture music between 1920 and 1960, even rising to number three on the national charts in 1927 ("The Sweetheart of Sigma Chi," n.d.a). The extensive recording of the song is significant because it signaled the entrance of one of the first popular culture representations of the sweetheart image into the American consciousness. Suddenly, women who had never stepped foot on a college campus were being exposed to an idealized, feminine image that permeated campus culture during much of the early to mid-twentieth century. The sweetheart image found both on campus and within popular culture promoted a form of femininity that aligned with older nineteenth century views that regulated a woman's position in society within the domestic sphere but did not strictly conform to Victorian views, incorporating newly developed beliefs about femininity as well. In this article the author contends that the image of the sweetheart gained prominence within popular culture during the early-twentieth century as a response within American society to the increase of women entering higher education during the period. He highlights the shifting role of women within society and higher education during the early-twentieth century and depicts the manner in which the sweetheart image within popular culture attempted to promote a hyper-feminized, restrictive form of femininity in response to the changing nature of women's roles in American society. Through this analysis, a clear picture develops that depicts the sweetheart image found within popular culture as a tool to challenge the realities of the changing roles for women in higher education.