With the exception of this marriage before a huge congregation, Cullen was a shy person. He was not flamboyant with any of his relationships. It was rumored that Cullen had developed a relationship with Harold Jackman, "the handsomest man in Harlem", which contributed to Cullen and Yolande's 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 evidence that the men were lovers, despite newspaper stories and gossip suggesting the contrary. 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.