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The female figures of Lady Wisdom and Dame Folly, found in the postexilic Wisdom literature, have always attracted much debate and speculation. The questions of who they are and what they stand for, particularly in the case of Lady Wisdom, have been hotly debated. Is she merely a literary creation, driven by the fact that the nouns for wisdom in Hebrew and Greek, חכמה and σοφία, are feminine in gender? Or is she an actual divine figure, a female hypostasis of Yahweh, the god of Israel, indicating a female divine presence in Israelite religion? These debates have yet to be resolved. Now that the large corpus of sapiential texts from Qumran is beginning to be studied, new light may be shed on the figures of Lady Wisdom and Dame Folly. This paper investigates these two figures in three Qumran texts: 4Q184, “The Wiles of the Wicked Woman,” 4Q185, “A Sapiential Work,” and 4Q525, “Beatitudes,” to see whether the presentation of these figures in three otherwise unknown texts can shed any light on their function in Second Temple Jewish thought.