Are faith and doubt in essential conflict? Or are they intimate friends, elevating and refining one another? Should a religious life, focused on faith in God, be one blessedly free from the existential doubt that can plague those who live without religion in their lives? Or should faith in God, which can so easily be pushed to the extreme, and harnessed for nefarious purposes, be tempered with healthy doses of doubt and uncertainty? We explore such questions, through traditional texts and through what is present in our own minds and hearts, as we get ready for a very faith-focused season in the Jewish calendar.