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In August 1932, when nineteen-year-old Hadassah Kaplan learned that she would no longer be able to teach in the New York public school where she had been a substitute teacher, she decided, instead, to travel to Mandatory Palestine. Her parents, including the founder of Reconstructionist Judaism, Mordecai Kaplan, agreed that she should spend the year studying Hebrew and exploring Palestine's capacity to revitalize Judaism as a civilization. Within her first month abroad, Hadassah began corresponding with her father in Hebrew. This note includes an exchange of Hebrew letters between Mordecai and Hadassah in which he articulated his loneliness as he sought to revitalize Judaism in the United States. He asked Hadassah if "a man like me [should] settle in the Land of Israel?" She shared her father's question with two of his friends, the Hadassah founder Henrietta Szold and the Zionist educator Jessie Sampter, who expressed reservations about Kaplan migrating. But Hadassah liked the idea. She argued that this was a place where he could pursue his own happiness, having already done enough for the "spiritual state" of the Jewish people. The discussion between father and daughter offers insight into their reflections on what role the Hebrew language and the Land of Israel should play in their personal lives as well as for the Jewish people more generally. Within the year, Hadassah returned to New York where she and her father lived most of their lives. Nevertheless, each remained committed to Hebrew and Zionism, with Mordecai briefly settling in Israel after retiring in the mid-1970s.