Amid the theatrical grandeur of The Life of a Showgirl, one track—“Ruin the Friendship”—unexpectedly delivers a poignant moment. Susan Lang, speaking to the Tennessean after the album’s release, says the song evokes memories of her son Jeffrey, who was a classmate of Swift’s.

In the Tennessean interview published following the record’s debut, Lang described hearing the sixth track for the first time and the emotions it stirred. Her son attended Hendersonville High School with Taylor Swift and later studied biology at the University of Tennessee at Chattanooga before his sudden death in 2010.

“They were really good friends,” Lang said. “That’s rare these days. They hung out at her house a lot. They were always joking around with each other.”

Musically, “Ruin the Friendship” begins as a wistful recollection of teenage crushes and familiar camaraderie, then moves into a sobering turn in its later verse when the narrator learns of a tragic loss. In the final refrain Swift quietly reflects on missed chances, softly repeating the line, “Should’ve kissed you anyway.”

Lang told the Tennessean she was moved that Swift still remembers her son decades later, saying it’s “bittersweet” that his name remains alive through the song. “She’s keeping his name alive,” Lang added.

Released on Oct. 3, The Life of a Showgirl launched to enormous commercial success: the album sold more than four million copies during its first seven days, establishing a new opening-week record in the modern era and surpassing Adele’s previous benchmark.

Although Swift has not publicly confirmed whether “Ruin the Friendship” was inspired by Jeffrey, fans quickly connected the lyrics to him. A photograph circulating online shows a teenage Swift posing with the late classmate, which further fueled speculation.

Listen to “Ruin the Friendship” below.

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