Taylor Swift’s “Ruin The Friendship” Lyrics Illustrate A Devastating Regret

When Taylor Swift’s The Life of a Showgirl tracklist was revealed, Swifties immediately began theorizing about the lineup’s titles — with much speculation surrounding the track, “Ruin the Friendship.” 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.

Nostalgic Pangs

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.”

While Swift has several songs that channel young love and crushes — from “Hey Stephen” to “You Belong with Me” — her latest applies a particularly mature, heart-wrenching twist to the topic. After leaving school, she sings in the bridge, “Abigail called me with the bad news. Goodbye, and we’ll never know why.”

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.”

While the specific subject of “Ruin the Friendship” may not be clear, Swift has previously opened up about losing a friend. “Yesterday, I sang at the funeral of one of my best friends, and he was 21,” Swift said at the 2010 BMI Country Awards. “And I used to play my songs for him first. So I would like to thank Jeff Lang — and as always, all the creative minds in this room who inspire me every day.”

Taylor Swift’s “Ruin The Friendship” Lyrics

Read the full lyrics to Swift’s new song below.

Glistening grass from September rain

Gray overpass full of neon names

You drive 85

Gallatin Road and the lakeside beach

Watching the game from your brother’s Jeep

Your smile, miles wide

And it was not an invitation

Should’ve kissed you anyway

Should’ve kissed you anyway

And it was not convenient, no

But your girlfriend was away

Should’ve kissed you anyway

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 shoulder, catch a glimpse

And see you looking at me

And it was not an invitation

But as the 50 Cent song played

Should’ve kissed you anyway

And it was not convenient

Would’ve been the best mistake

Should’ve kissed you anyway

Don’t make it awkward in second period

Might piss your ex off

Lately we’ve been good

Staying friends is safe

Doesn’t mean you should

Don’t make it awkward in second period

Might piss your ex off

Lately we’ve been good

Staying friends is safe

Doesn’t mean you should

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”

And it was not an invitation

Should’ve kissed you anyway

Should’ve kissed you anyway

And it was not —

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

Should’ve kissed you anyway

Should’ve kissed you anyway