
"Swift constructs "Ruin the Friendship" around high school memories, like driving around Nashville and going to prom. Specifically, she reflects on moments with a friend who had a "miles-wide" smile, someone who could have been something more. In hindsight, she wishes she had acted on her feelings even if they weren't "convenient" or sensible at the time. "Would've been the best mistake," she sings. "Should've kissed you anyway.""
"Would it recall a falling out with a high-profile pal, or perhaps serve as a playful ode to making the first move? As it turns out, neither. The "Ruin the Friendship" lyrics explain Swift's journey with loss and regret. The song's warm, balmy sound belies its arrival as one of the most heartbreaking entries in her oeuvre."
"Swift says she returned home "with so much left to say," but could only tell her friend at his grave: "Should've kissed you anyway." She concludes the song with advice for her listener, urging them to "ruin the friendship" rather than regret it and wonder "for all time.""
The song "Ruin the Friendship" centers on high school memories—driving around Nashville, going to prom—and reflects on a friend with a "miles-wide" smile who might have become more. The narrator regrets not acting on romantic feelings, calling a would-have-been kiss "the best mistake." A bridge reveals a sudden death: "Abigail called me with the bad news," leaving the narrator to return home with "so much left to say" and only confess at the friend's grave. The warm, balmy production contrasts the heartbreak, and the song advises choosing to "ruin the friendship" rather than live with perpetual regret.
Read at Bustle
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