Pope John Paul II, in Fides et ratio#108, states that there is a deep harmony between the vocation of true philosophy and the Blessed Virgin Mary. This intriguing claim, so different from the usual link of Mary with faith, is developed in this article. Drawing analogical implications from selected events in Mary's life, two questions will be asked: How do philosophers “philosophize in Mary?;” and how could this way of philosophizing help us today to renew the vocation to be a philosopher? The following authors are considered: Thomas Aquinas, Edith Stein, Jacques and Raïssa Maritain, Bernard Lonergan, Josef Ratzinger, Mary Daly, Robert Sokolowski, Norris Clarke, Søren Kierkegaard, Karol Wojtyla, John Paul Sartre, Simone de Beauvoir, Judy Chicago, and John Henry Newman.