A naive and idealistic 22-year-old from the Midwest, Adrienne Miller got her lucky break when she was hired as an editorial assistant at GQ magazine in the mid-’90s. Three years later, she forged her own path, becoming the first woman to take on the role of literary editor of Esquire. This was also a unique moment in history that saw the rise of a new literary movement, as exemplified by McSweeney’s and the work of David Foster Wallace. The mercurial Wallace would become the defining voice of a generation and the fiction writer Miller would work with most. Their intellectual and artistic exchange grew into a highly charged professional and personal relationship between the most prominent male writer of the era and a young woman still finding her voice.