During 1923 to 1931 bennett started a support group that place for the young writers of harlem that provided sustained association with their peers inculded in this group was Langston Hughes,Countee Cullen,Eric Walrond,Helene Johnston,Zora Neale Hurston
In 1940, she married educator and writer Richard Crosscup who was of European ancestry. 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 Artist Guild in 1935, and the Harlem Community Art Center was under her leadership from 1939 to 1944.During this time, she was also active on the board of the Negro Playwright's Guild and involved with the development of the George Washington Carver Community School.
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, Crosscup, to the small town of Kutztown, Pennsylvaniawhere they opened an antique shop. called Buttonwood Hollow Antiques. Her husband died in 1980, due to heart failure, as well as Bennett who died of cardiovascular on May 30, 1981, at the Reading Hospital in Reading, Pennsylvania.