After marrying Dr. Albert Joseph Jackson in 1927, Bennett resigned from Howard University as the school's administration disapproved of their relationship. That same year, the couple moved to Eustis, Florida. Her time in Florida had a negative impact on her work as it was too far from Harlem to promptly receive news for her to write about in her column for Opportunity.
Due to the racism they encountered and their town's financial problems, they remained in Florida for only three years and moved to Long Island in 1930. Bennett began to write more frequently after working with the Federal Writers Project and Federal Art Project. After losing their home in Long Island, Jackson died in 1936, and Bennett moved back to New York.[1][24]
In 1940, she married educator and writer Richard Crosscup, who was of European ancestry.[25] Their interracial marriage was not socially acceptable at Bennett's time. Harlem remained Bennett's passion, however, and during the late 1930s and the 1940s she remained in the arts. She served as a member of the Harlem Artists Guild in 1935, and the Harlem Community Art Center was under her leadership from 1939 to 1944.[1]
During this time, she was active on the board of the Negro Playwright's Guild and involved with the development of the George Washington Carver Community School.[26][27] In 1941, the FBI continuously investigated Bennett on suspicion that she was a Communist and continued to do so on and off until 1959 despite no conclusive or evidential findings. However, this experience caused her to remove herself from the public eye and she began working as a secretary for the Consumers Union.
Bennett retired in 1968 and moved with her husband, Richard Crosscup, to Kutztown, Pennsylvania, where they opened an antiques shop called Buttonwood Hollow Antiques.[1]
