Cullen married Yolande Du Bois on April 9, 1928. She was the surviving child of W. E. B. Du Bois and his first wife Nina Gomer Du Bois, whose son had died as an infant.[17] The two young people were said to have been introduced by Cullen's close friend Harold Jackman.[18] They met in the summer of 1923 when both were in college: she was at Fisk University and he was at NYU.[19] Cullen's parents owned a summer home in Pleasantville, New Jersey near the Jersey Shore, and Yolande and her family were likely also vacationing in the area when they first met.[19]
While at Fisk, Yolande had had a romantic relationship with the jazz saxophonist Jimmie Lunceford.[20] However, her father disapproved of Lunceford. The relationship ended after Yolande accepted her father's preference of a marriage to Cullen.[20]
The wedding was the social event of the decade among the African-American elite. Cullen, along with W.E.B. Du Bois, planned the details of the wedding with little help from Yolande.[17] Every detail of the wedding, including the rail car used for transportation and Cullen receiving the marriage license four days prior to the wedding day, was considered big news and was reported to the public by the African-American press.[17] His father, Frederick A. Cullen, officiated at the wedding.[21] The church was overcrowded, as 3,000 people came to witness the ceremony.[17]
After the newly wedded couple had a short honeymoon, Cullen traveled to Paris with his guardian/father, Frederick Cullen, and best man Jackman.[22] Yolande soon joined him there, but they had difficulties from the first.[21] A few months after their wedding, Cullen wrote a letter to Yolande confessing his love for men.[23] Yolande told her father and filed for divorce.[21] Her father wrote separately to Cullen, saying that he thought Yolande's lack of sexual experience was the reason the marriage did not work out.[24] The couple divorced in 1930 in Paris.[21] The details were negotiated between Cullen and Yolande's father, as the wedding details had been.[17][25]
With the exception of this marriage before a huge congregation, Cullen was a shy person. He was not flamboyant with any of his relationships.[23] It was rumored that Cullen had developed a relationship with Jackman, "the handsomest man in Harlem", which contributed to Cullen and Yolande's divorce.[23] The young, dashing Jackman was a school teacher and, thanks to his noted beauty, a prominent figure among Harlem's gay elite. According to Thomas Wirth, author of Gay Rebel of the Harlem Renaissance, Selections from the Work of Richard Bruce Nugent, there is no evidence that the men were lovers, despite newspaper stories and gossip suggesting the contrary.[23] Scholars have not reached consensus on Cullen's sexuality. He married Ida Mae Roberson in 1940 and lived, apparently happily, with her until his death.
Jackman's diaries, letters, and outstanding collections of memorabilia are now held in various depositories across the country, such as the Amistad Research Center at Tulane University in New Orleans and Atlanta University (now Clark Atlanta University) in Atlanta, Georgia. At Cullen's death, Jackman requested that his collection in Georgia be renamed, from the Harold Jackman Collection to the Countee Cullen Memorial Collection, in honor of his friend. After Jackman died of cancer in 1961, the collection at Clark Atlanta University was renamed as the Cullen-Jackman Collection to honor them both.[26][27]
