Robert Sheffield (b. 1966) is an American music journalist, known best as a frequent contributor to Rolling Stone. Originally from Massachusetts, Sheffield attended Yale University as an undergraduate and then pursued graduate studies at the University of Virginia before eventually settling in Brooklyn, New York. He has published books on a wide variety of artists and genres, including Duran Duran, David Bowie, and the Beatles. His first book, Love is a Mixtape: Life and Loss, One Song at a Time (2007), follows his relationship with his first wife, Renée Crist, who died suddenly, only five years into their marriage, when Sheffield was 31.

Sheffield has been an avid listener to Taylor Swift since 2007, when he happened to hear “Our Song,” the third single from Swift’s self-titled debut album, playing during an advertising break on the CW. He writes that the song’s lyrics were immediately captivating to him, and that he was surprised to learn that they were written and performed by such a young newcomer to the industry. Heartbreak follows the development of his close personal relationship with her music since that moment. Sheffield’s authorial voice throughout the text, therefore, is multifaceted; he speaks both with the authority of a well-established music journalist, and with the personal enthusiasm of a fan.