Handy attended North Division High School (now Lincoln Park High School) in Chicago, and then the University of Michigan during the 1902–03 academic year. During that time he was working as a campus correspondent for the "Chicago Tribune" when on May 8 he wrote an article about a lecture in the Elocution 2 class given by Prof. Thomas C. Trueblood as a "course in lovemaking." Handy went on to describe how Trueblood had dropped to a bended knee in order to demonstrate how to make an effective marriage proposal. John T. McCutcheon, a "Chicago Record Herald" cartoonist, followed the next day with a cartoon about a "Professor Foxy Truesport" showing his class how to best make love.