This study examines the attribution of abstract values to women by analyzing four characters spanning literary genres and more that 2000 years. Penelope, Macrina, Philosophia, and Beatrice are connected by their contribution to the theme of wisdom through their use of reason against passion. Feminine personification of reason and wisdom makes its own contribution as antidote to traditional understanding of 'feminine' as 'emotional' or 'irrational'. This book examines allegorical personification of Sophia, or wisdom, in ancient and medieval philosophy and literature, examining four feminine figures who personify wisdom. The first is Penelope of Homeric epic, weaving and unraveling to forestall her suitors; the tale is interpreted allegorically by Cynics and Stoics to discuss the place of logic in philosophy. The second example, Macrina, sister of Gregory of Nyssa, is less obviously allegorical. But Gregory depicts her as an embodiment of wisdom using the theme, 'reason against passion'. Boethius' Philosophia is portrayed as the lady who consoles as she reminds the prisoner of divine reason ruling the world. And finally, Dante's Beatrice, his muse, teacher and guide in achieving the beatific vision. Contemporary recognition of allegory as rhetorical technique supports appreciation of Dante's skill in depicting Beatrice as Lady Wisdom.