By 1928, Caspary was writing for "Gotham Life: the Metropolitan Guide", a free entertainment guide distributed through hotels. This job provided free tickets to theater shows, concerts, and nightclubs and introduced her to a wide circle of press agents and celebrities. While at "Gotham Life", she had lived under an assumed name in a "working girl's home". In March 1929, she again quit her job to write full time, and her 1930 novel "Music in the Street" was set in a working girl's home. Moving back to Chicago, she co-wrote the play version "Blind Mice" with Winifred Lenihan, which featured an all-female cast and formed the basis for the 1931 film "Working Girls". She and her mother moved to Connecticut to do the rewrites on the play. The play was disastrous – Caspary's inexperience with the process caused her to take everyone's advice, altering the play's text constantly. When she and Lenihan weren't present, the producers even rewrote the play themselves. When Caspary returned, the true original copy could not be found and the play closed in two weeks.