1938 the University of Wisconsin awarded him the degree in absentia; presumably the school wanted to recognize his fame. As a young man Fearing was thin, with dark hair and skin, and liked to wear dark suits. His voice was low and lispy. He had a "little-boy appeal", with messy hair and habits, horn-rimmed glasses, and an immature disposition—some of which may be seen in Alice Neel's oil portrait, painted in 1935, which is now at the Museum of Modern Art in New York. The portrait includes some references to Fearing's poetry and shows a small skeleton in his chest, grasping his heart and pouring blood from it; Neel commented that "He really sympathized with humanity ... His heart bled for the grief of the world." After his death, according to Robert M. Ryley, friends remembered "his charm, his eloquence, his almost courtly manners, his prickly independence, his not-quite-hidden vulnerability and innocence—but mostly they would remember his gloomy, sardonic skepticism". During the late 1920s he had a romantic relationship with the writer and activist Margery Latimer, whom he met at Wisconsin. (Latimer's roman à clef This Is My Body includes a character based on Fearing.) Fearing cheated on Latimer and never proposed to her; she rejected his later attempt to renew their relationship. In 1931, he met Rachel Meltzer, a nurse by training and a medical social worker. Fearing was poor at expressing affection in person (if not in his letters) and less interested in marriage than Meltzer. She later said of her husband, "Kenneth spent his whole life hiding his inner self from other people"; "[he] needed someone to take care of him." They were married on April 26, 1933, and their son, Bruce Fearing, was born on July 19, 1935. The family soon travelled to Europe for nine months thanks to the $2,500 that came with Kenneth's 1935 Guggenheim Fellowship. Partly due to Fearing's growing alcoholism, he and Rachel divorced in 1941, with Rachel having custody of their son. He stayed at the Yaddo artists' retreat for the first time in 1938 and returned often. At Yaddo he began a relationship with the painter Nan Lurie and they married on June 18, 1945. In this period his drinking became dangerous to his health, which scared him into temperance. Nan found him duller as a result, and their relationship suffered. They separated in 1952. This was his last marriage.