The indisputable “queen of crosswords,” Anna Shechtman published her first New York Times puzzle at age nineteen, and later, spearheaded the The New Yorker’s popular crossword section. Working with a medium often criticized as exclusionary, elitist, and out-of-touch, Anna is one of very few women in the field of puzzle making, where she strives to make the everyday diversion more diverse. She excavates the hidden history of the crossword and the overlooked women who have been central to its creation and evolution, from the “Crossword Craze” of the 1920s to the role of digital technology today. As she tells the story of her own experience in the CrossWorld, she analyzes the roles assigned to women in American culture, the boxes they’ve been allowed to fill, and the ways that they’ve used puzzles to negotiate the constraints and play of desire under patriarchy.