Suffering is at the core of Jewish-American literature in general and in the fiction of Saul Bellow and Chaim Potok in particular. Bellow and Potok, affirmative writers who believe in man’s redemption through suffering, portray characters that evoke the Job-like “suffering man” whose endurance and faith in God are finally rewarded. “Schooling in grief,” a phrase borrowed from Bellow’s Herzog (1964), can also be applied to Bellow’s The Victim (1947) and Potok’s The Chosen (1967). The paper reads these two novels with the notion of the I/It and I/Thou relationship as explained in Martin Buber’s I and Thou (1923). The characters in The Victim and The Chosen move from the I/It to the I/Thou encounter through suffering, which eventually leads towards mutual understanding and love for the other.