I think the enterprise is a very worthy one, and I think you have selected for it the very best short story that I have ever written... [I] shall be glad if I shall help to make your worthy venture successful.
Originally published in 1899 in his collection of Stories of the Color Line, "The Wife of His Youth" remains one of Chesnutt's most well-known stories. The story tells of a social organization coincidentally made up of "colored persons" who were "more white than black" (much like Chesnutt himself). The joke was that membership was only granted to those whose skin tone was light enough to show blue veins — hence their nickname, the Blue Vein Society. Mr. Ryder, the de facto leader of the group, organizes a ball with the hope of proposing to a beautiful (and much, much younger) woman. But, just before the event begins, he is visited by a strange, dark-skinned elderly woman, a remnant of the days "before the war."
In typical Chesnutt fashion, the story carefully carves up racism with a scalpel. The most positive qualities recognized in the story are those which make black people seem more white (nearly straight hair, in addition to pale complexion, as well as a prejudice against people who were not born free). The struggle for the black population, including those who were partly white, was to either maintain their separate identity, or fully assimilate into white culture. In presenting this dilemma, Chesnutt also asks the question: Can African Americans ever forget their collective past of enslavement?