This essay examines the ways in which women lawyers of two generation–the pioneer generation of the 1880s and the “new woman” generation of the 1910s–confronted the dilemma of marriage and career. Members of the Equity Club in the 1880s revealed three distinct sets of attitudes toward balancing marriage and career: the separatist approach that a professional woman must remain single; the Victorian attitude that a married woman must sacrifice her career; and the integrated approach that a woman could have both marriage and career. Women lawyers surveyed by the Bureau of Vocational Information in 1920 revealed that the “new woman” generation of women lawyers lived in an era of transition. While they shared the same separatist, Victorian, and integrated views toward marriage and law practice as did women lawyers in the 1880s, they also embraced the new values of the early 20th century which shaped both the contours of the legal profession and the parameters of women's lives. Set within the context of the new values of the era, the separatist, Victorian, and integrated approaches to resolving the dilemma of marriage and career, which were originally formulated by women lawyers in the late 19th century, assumed new meanings for women lawyers in the early 20th century.