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Inside Taylor Swift's 'Ruin the Friendship,' Her Most Nashville Track on New Album

Taylor Swift reflects on a lost high school romance and urges acting on feelings to avoid lifelong regret, inspired by the death of a close friend.

  • On Friday, October 3, Taylor Swift released The Life of a Showgirl, which includes 'Ruin the Friendship' as track 6.
  • Swift wrote the song from personal experience, exploring regret about not kissing a boy who later died, based on memories shared by longtime friend Abigail Anderson Berard during the European leg of the 2024 Eras Tour.
  • Grounded in Hendersonville details like Gallatin Pike, the song references driving 85 and scenes from Hendersonville High School prom to a graveside visit where Swift whispers `Should've kissed you anyway`.
  • Fans speculated online that Blake Lively was the target, but reporting shows Swift revisits memories of Jeff Lang, her high-school friend who died in 2010.
  • Swift urges listeners to 'ruin the friendship' rather than live with regret, blending warm nostalgia with darker undertones that fans find relatable about secret crushes.
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  • 64% of the sources lean Left
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The Tennessean broke the news in Nashville, United States on Friday, October 3, 2025.
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