A young mother goes astray. Or does she? Let AI decide? Decide yourself. Inspired by the short story A Pair of Silk Stockings by Kate Chopin, the play comprises a thought-provoking double story: a professor and student in the present re-enact the adventures in 1897 St. Louis of a young woman taking a day off from her family responsibilities. The drama explores contemporary versus historical visions of the role of women in society. It encourages the audience to consider their own conclusions about the mother’s actions while illustrating the importance of empathetic imagination and critical thinking given current claims about the value of Artificial Intelligence as an interpretive tool.