This article investigates whether Philo and the rabbis were intrigued by the same problems in the Biblical text and how they solved them. Three sets of questions and answers are studied, pertaining to the trees of Life and Knowledge as well as to God's famous saying “let us make man” (Gen. 1:26). Each cluster is investigated in its historical context and in comparison to its parallel in the other corpus. Philo and Genesis Rabbah operated in radically different environments. While Philo was directly familiar with Homeric scholarship and applied certain of its methods to Scripture, Genesis Rabbah emerged in an environment where Christian exegetes rivaled their study of the same text. Questions and answers were now raised concerning the same verses and helped to define boundaries between the different groups.