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Sexuality
Cullen was first brought to the idea of his sexuality from the help of American writer, Alain Locke. Locke wanted to introduce a new generation of African American writers, like Countee Cullen. Locke sought to present the authentic natures of sex and sexuality through writing, thus creating relationships with those that felt the same. Cullen looked to Locke for any advice and guidance, thus developing a father-and-son like relationship. Locke helped Cullen accept his sexuality, exposing him to gay-affirming material, like the work of Edward Carpenter. In March 1923, Cullen had written in a letter to Locke: “It opened up for me soul windows which had been closed; it threw a noble and evident light on what i had begun to believe, because of what the world believes, ignoble and unnatural”.

Relationships
Cullen married Yolande Du Bois in April 1928, the only surviving child of W.E.B. Du Bois. It is said that they were introduced by Cullen’s close friend Harold Jackman. The wedding was the social event of the decade. Every detail of the wedding was considering big news and was published to the public by the African American press. A few months after their wedding, Cullen had written a letter to Yolande confessing his love for men. The couple then divorced in 1930.

With an exception to his first marriage, Cullen was a shy person and was not flamboyant with any of his relationships. It was rumored that Cullen developed a relationship with Harold Jackman, "the handsomest man in Harlem", which contributed to Cullen and Du bois’ divorce. 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 concrete proof that they ever were lovers, despite newspaper stories and gossip suggesting the contrary (find citation).

Jackman's diaries, letters, and outstanding collections of memorabilia are 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 the name of the Georgia accumulation be changed from the Harold Jackman Collection to the Countee Cullen Memorial Collection in honor of his friend. When Jackman, himself, succumbed to cancer in 1961, the collection was renamed the Cullen-Jackman Collection to honor them both.