Taylor Swift’s ‘Ruin the Friendship’ Lyrics Describe the Romantic Regret That Haunts Her

THE RUNDOWN

• Taylor Swift’s “Ruin the Friendship” lyrics explore a romantic regret she still holds from her high school days.
• Swift sings about wishing she had kissed a friend who later passed away.
• The singer has spoken before about losing a close high school friend, Jeff Lang, in her early 20s.

While many fans originally theorized that the Life of a Showgirl track “Ruin the Friendship” would be about Taylor Swift’s relationship with Blake Lively, it turns out, Swift actually had someone else in mind. The song takes listeners back to her high school days and describes her regret of not kissing a friend who later passed away.

She sings about learning of his loss from her longtime friend Abigail Anderson: “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 it at the grave / ‘Should’ve kissed you anyway.’”

Swift revisits this message at the end of the song, advising others not to make her same mistake: “My advice is always ruin the friendship / Better that than regret it / For all time / Should’ve kissed you anyway / And my advice is always answer the question / Better that than to ask it / All your life.”

So who was this friend? Swift doesn’t explicitly name him, but she did lose a close high school friend in her early 20s. At the 2010 BMI Country Music Awards, the then 20-year-old singer spoke about the death of Jeff Lang while accepting the Country Songwriter of the Year award. She attended the ceremony on Nov. 9, 2010, just one day after his funeral. He had passed away on November 2, according to a memorial database. Days before, Swift had released her album Speak Now on Oct. 25, 2010.

“Yesterday, I sang at the funeral of one of my best friends,” she told the crowd. “And he was 21, and I used to play my songs for him first. So I would like to thank Jeff Lang.” Fans believe Swift was also singing about Lang on her Red vault track “Forever Winter,” which details her concern for a friend struggling with mental health and substance use.

“Ruin the Friendship” is one of Swift’s most emotional tracks on The Life of a Showgirl. Read its lyrics in full and listen to the song below:

Verse 1Glistening grass from September rainGray overpass full of neon namesYou drive (Mm-mm), 85 (Mm-mm)Gallatin Road and the lakeside beachWatching the game from your brother’s Jeep

Your smile (Mm-mm), miles wide

Chorus

And it was not an invitationShould’ve kissed you anywayShould’ve kissed you anywayAnd it was not convenient, noBut your girlfriend was away

Should’ve kissed you anyway, hey

Verse 2

Shiny wood floors underneath my feetDisco ball makes everything look cheapHave fun (Mm-mm), it’s prom (Mm-mm)Wilted corsage dangles from my wristOver his shoulder, I catch a glimpseAnd see (Mm-mm)You looking at me

Chorus

And it was not an invitationBut as thе 50 Cent song played (Song played)Should’vе kissed you anyway (Anyway)And it was not convenient, no (It was not, convenient)Would’ve been the best mistakeShould’ve kissed you anyway, hey

Refrain

Don’t make it awkward in second periodMight piss your ex off, lately we’ve been goodStaying friends is safe, doesn’t mean you shouldDon’t make it awkward in second periodMight piss your ex off, lately we’ve been good

Staying friends is safe, doesn’t mean you should

Bridge

When I left school, I lost track of youAbigail called me with the bad newsGoodbye, and we’ll never know whyIt was not an invitationBut I flew home anywayWith so much left to sayIt was not convenient, noBut I whispered at the grave

“Should’ve kissed you anyway”

Chorus

Oh, and it was not an invitation (It was not, an invitation)Should’ve kissed you anyway (Anyway)Should’ve kissed you anyway, anyway (Anyway)

Post-Chorus

And it was not—My advice is always ruin the friendshipBetter that than regret it for all timeShould’ve kissed you anywayAnd my advice is always answer the questionBetter that than to ask it all your lifeShould’ve kissed you anyway

Should’ve kissed you anyway