All people who applied for poor relief have been subject to negative moral judgments going back to the early Anglo-American poor laws which enshrined the idea that there are “worthy” and “unworthy” poor. But even within this highly moralistic arena, women who entered the almshouse pregnant were subject to labeling as either “seduced,” and hence blameless, or as “loose” women who had sought out sexual relations and hence could be punished and vilifi ed. Women who were judged immoral could be imprisoned in a workhouse or house of correction, although gradually reformers created “homes for fallen women” under a variety of names. This chapter will review the Victorian drama, which, in the earlier years of the almshouse (roughly until the late 1870s), shaped both the description and treatment of women and the hunting down of the putative fathers through “bastardy proceedings.” I will then describe how the records and other data about the actual relations between poor and working-class women and men tend to be far less dramatic than the Victorian rhetoric. Finally, for women we have information about, we will explore what became of the unmarried mothers who entered the Tewksbury Almshouse.