Weiss graduated from Public School #77. He later enrolled at the High School of Commerce where he learned shorthand and how to type; however, he felt that he did not benefit much from the available courses. His grades began to fall, and with a little encouragement from his mother, he eventually dropped out of high school. After working many odd jobs, Weiss enrolled at the College of the City of New York in 1924. He took free night classes in philosophy, graduating cum laude in 1927. At the College of the City of New York, he studied with Morris R. Cohen, who awakened in him an interest in the American pragmatist and logician Charles Sanders Peirce. During this period he also met Victoria Brodkin (d. 1953), whom he would later marry on October 27, 1928. They had two children: Judith, who was born in 1935, and Jonathan, who was born in 1939.