Created by Abraham Cahan in 1906, the advice column A Bintel Brief ran as the most enduring feature of the New York Yiddish newspaper Forverts for over seven decades. This study takes a closer look at the letters and responses to A Bintel Brief thereby revealing the hardships of uprooted Eastern European Jews. In an uncharted environment they turned to the column for guidance. In his answers, the editor of The Bintel Brief was always sympathetic, yet pragmatic, encouraging assimilation and ethnic group solidarity, thus paving the way for the readers to become accepted Jewish Americans.