Who Is Taylor Swift’s ‘Ruin The Friendship?’ About? The Devastating True Story Behind The Song

Taylor Swift’s The Life Of The Showgirl is officially out in the world, and fans have been going rabid analyzing the new lyrics. But there’s one song in particular that’s a storytelling rollercoaster, especially if you pay close attention to the lyrics.

“Ruin The Friendship” is the sixth song of an album that’s full of love songs, so it doesn’t stand out much at first—except for the fact that unlike the other songs that seem to be rooted in this moment of Swift’s life, this one takes us back to high school imagery, to falling in love during the shy, awkward periods of life. This isn’t a Travis Kelce love song. In fact, the lyrics are pretty plainly about the teen years:

“Shiny wood floors underneath my feet / Disco ball makes everything look cheap / Have fun, it’s prom / Wilted corsage dangles from my wrist / Over his shouldеr, I catch a glimpse / And see (Mm-mm) you lookin’ at me”

Throughout the song, Taylor expresses her regret about choosing “not to ruin the friendship,” saying again and again, “It was not an invitation, should’ve kissed you anyway.” The song is cute and almost juvenile in a way that feels nostalgic, evoking a past Taylor we’ve all seen before, but the lyrics take a sudden turn in the second half of the song:

“When I left school, I lost track of you / Abigail called me with the bad news / Goodbye, and we’ll never know why / It was not an invitation / But I flew home anyway / With so much left to say / It was not convenient, no / But I whispered at the grave / ‘Should’ve kissed you anyway'”

Fans excited to hear a call-out to Taylor’s high school best friend Abigail (famously sung about in Swift’s song “Fifteen”) quickly changed their tune as the big reveal hit: This high school crush was someone who had later died, and that the song is about regret on a deeper level—and about grief.

So who is Taylor Swift talking about here? Believe it or not, this isn’t just some fictional story like what she wrote about during the Folklore era. It’s actually most likely about the same friend she wrote about in her Red (taylor’s version) vault track “Forever Winter”.

In “Forever Winter,” a younger Taylor writes about reaching out to a friend who’s having a difficult time and clearly under the influence of substances. In the chorus, she sings:

“I didn’t know / You were breakin’ down / I’d fall to pieces on the floor / If you weren’t around / Too young to know it gets better / I’ll be summer sun for you forever / Forever winter if you go”

Both songs are seemingly about Swift’s high school friend Jeff Lang, who died of an overdose in 2010 after struggling with mental health issues.

By the end of “Ruin The Friendship,” Taylor imparts one last piece of wisdom:

“My advice is to always ruin the friendship / Better that than regret it for all time / Should’ve kissed you anyway / And my advice is to always answer the question / Better that than to ask it all your life / Should’ve kissed you anyway.”