Sheffield acknowledges throughout Heartbreak that he is not a typical member of Taylor Swift’s audience, which generally skews towards women and girls. How does his perspective as a male music critic inform his interpretation of Swift’s music and career?

In Heartbreak, Sheffield meticulously contextualizes Swift’s discography in the landscape of music history. Explore one of the connections between Swift and other artists mentioned throughout the book in further detail, conducting your own research and elaborating upon Sheffield’s observations.

Do you have a favorite Taylor Swift song? If so, how do its lyrics and context fit into Sheffield’s broader narrative of Swift’s career and artistry? Who is the persona who speaks in the song, and how does this persona or character participate in a conversation with the speakers of other Swift songs?