Cummings was married briefly twice; his longest relationship was outside marriage. Cummings's first marriage, to Elaine Orr, began as a love affair in 1918 while she was married to Scofield Thayer, one of Cummings's friends from Harvard. During this time he wrote a good deal of his erotic poetry. The couple had a daughter together, Nancy, born on December 20, 1919. Nancy was Cummings's only child.
After divorcing Thayer, Elaine married Cummings on March 19, 1924. However, they separated after two months and divorced less than nine months later. Elaine left Cummings for a wealthy Irish banker, moved to Ireland, and took Nancy with her. Under the terms of the divorce Cummings was granted custody of Nancy for three months each year, but Elaine refused to abide by the agreement. Cummings did not see his daughter again until 1946. Nancy later married Joseph Willard Roosevelt, second son of Kermit Roosevelt and Belle Wyatt Willard.
Cummings married his second wife Anne Minnerly Barton on May 1, 1929, and they separated three years later in 1932. That same year, Anne obtained a Mexican divorce; it was not officially recognized in the United States until August 1934.
The year Cummings and Anne separated, he met Marion Morehouse, a fashion model and photographer. Although it is not clear whether the two were ever formally married, Morehouse lived with Cummings in a common-law marriage until his death in 1962. She died on May 18, 1969, while living at 4 Patchin Place, Greenwich Village, New York City, where Cummings had resided since September 8, 1924.
According to his testimony in EIMI, Cummings had little interest in politics until his trip to the Soviet Union in 1931, after which he shifted rightward on many political and social issues. Despite his radical and bohemian public image, he was a Republican and, later, an ardent supporter of Joseph McCarthy.