Concluding my ranked list of the songs on Taylor Swift’s The Life of a Showgirl…
#1. ‘Ruin the Friendship’
There’s a school of thought that Taylor Swift has never been better than she was on 2008’s Fearless, an album released when she was 18 years old. And perhaps her best song is that album’s ‘Fifteen,’ written when she was just a couple of years older than its subjects.
I don’t necessarily subscribe to that theory — the woman has released a mountain of excellent material over the last 17 years — but I do viscerally respond to the authenticity and emotion Swift pours into her songs about high school.
Think about how beautifully she returned to those years on Folklore‘s ‘Betty’ (and the other two songs with which it forms a love triangle). Or the extended metaphor that drives the thorny ‘Miss Americana and the Heartbreak Prince.’
They say famous people get locked into the mindset of the age at which they become famous. Or maybe it’s just that those pre-fame years are the last normal ones a famous person ever has. Whatever the reason, Taylor Swift writes beautifully about high school, and this album provides another example.
‘Ruin the Friendship’ is about a friend who might have been something more had circumstances not gotten in the way. Years later, the young man dies (possibly by suicide) and Taylor looks back at their relationship wistfully. Given life’s fragility, why talk yourself out of following your heart?
This song is an odd fit for a spicy pop album about Swift’s newest and greatest romance. I’m not sure it belongs here, either lyrically or sonically. Minus the hindsight, it wouldn’t feel at all out of place on Swift’s early country-pop albums.
But I’m so glad it’s here. It’s always inspiring to discover a new favorite.
Glistening grass from September rain
Gray overpass full of neon names
You drive (Mm, mm)
Eighty-five (Mm, mm)
Gallatin Road and the Lakeside Beach
Watching the game from your brother’s Jeep
Your smile (Mm, mm)
Miles wide
[Chorus]
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
[Verse 2]
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 mе
[Chorus]
And it was not an invitation
But as the 50 Cent song played (Song playеd)
Should’ve kissed you anyway (Anyway)
And it was not (And it was not) convenient (Convenient), no
Would’ve been the best mistake
Should’ve kissed you anyway, hey
[Bridge]
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
[Verse 3]
When I left school, I lost track of you
Abigail called me with the bad news
Goodbye
And we’ll never know why
[Chorus]
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,” ooh
And it was not (It was not) an invitation (Invitation)
Should’ve kissed you anyway (Anyway)
Should’ve kissed you anyway (Anyway), anyway
And it was not—
[Post-Chorus]
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
[Outro]
Should’ve kissed you anyway
Meet Me In Montauk 
Having now had the opportunity to give this whole album a proper listen on our plane ride to Nashville, I found it to be quite good, and this song was certainly a standout.
very poignant lyrics 😢
Love her voice and writing on this song, totally understand why it’s a standout for you! Having this one feel the most out of place on the album keeps it a bit lower on my overall ranking.
Still sitting with some of these and I do really enjoy the whole album – it’s nice to have 12 tracks (even though I also absolutely loved the slew of Tortured Poets tracks).