Taylor Swift’s “Ruin the Friendship” Lyrics Meaning

Taylor Swift’s new song “Ruin the Friendship” is about wishing she’d kissed the secret crush she had on her friend, who has since passed.
The song seems personal verses fictional due to a reference to Taylor’s friend Abigail.
Taylor encourages listeners to kiss their crush and “ruin the friendship” before it’s too late.

Taylor Swift has done it again, writing a song that perfectly speaks to an experience most of can relate to: not acting on a friend crush due to fear of ruining said friendship.

Her new aptly titled song, “Ruin the Friendship,” is open to interpretation, but the lyrics are pretty self-explanatory as Tay sings about about wishing she’d kissed her friend. As the Grammy-winner puts it, “Should’ve kissed you anyway / And it was not convenient, no / But your girlfriend was away / Should’ve kissed you anyway.”

Tay’s story takes place in high school with references to prom and corsages, not to mention these lyrics: “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.”

We also know the song is based off personal experience thanks to a reference to her real-life high school best friend, Abigail, who told Taylor her former crush had passed. These emotional lyrics describe Taylor flying home for the funeral: “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.'”

Taylor ends the song with a message to listeners, saying “My advice is always ruin the friendship / Better that than regret it for all time.”

Check out the full lyrics here, via Genius:

Glistening grass from September rain
Gray overpass full of neon names
You drive (Mm-mm), 85 (Mm-mm)
Gallatin Road and the lakeside beach
Watching the game from your brother’s Jeep
Your smile (Mm-mm), 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, hey
Shiny wood floors underneath my feet
Disco ball makes everything look cheap
Have fun (Mm-mm), it’s prom (Mm-mm)
Wilted corsage dangles from my wrist
Over his shoulder, I catch a glimpse
And see (Mm-mm)
You looking at me
And it was not an invitation
But 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 mistake
Should’ve kissed you anyway, hey
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”
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)
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