Sunday, November 9, 2025

6. Ruin the Friendship


SPOILER ALERT! 

If you've never listened to this song before, please watch the video before you read today's blog.

1. Musical Style: '90s/'00s Alt-Pop Female

2. Literary References: Alfred, Lord Tennyson; 50Cent

3. Key Lyric: "My advice is always ruin the friendship / Better that than regret it for all time"

4. Favorite Lyric: "But I whispered at the grave / Should've kissed you anyway"

5. Taylor's Callback: "Fifteen," "You Belong With Me"

6. TL/DR: I wish I'd kissed that boy who died.

7. Previous Track 6s: The Outside, You Belong With Me, Mean, 22, Shake It Off, Look What You Made Me Do, I Think He Knows, mirrorball, no body no crime, Midnight Rain, But Daddy I Love Him.

Maybe the best song on the album, "Ruin the Friendship" is the tear-jerker, the song that will make Swifties cry every time they listen, and if you haven't heard the song yet, I've just spoiled it for you. Sorry about that. On the other hand, if you're this far into this blog series, you've probably heard the album as much as I have.

This song is most directly linked with her Fearless album in terms of both music and lyrics. The tune is dominated by jangly acoustic guitar, bringing back memories of her early career, with Martin and Shellback returning with their catchy drum-and-bass line that sounds like songs from that decade. 

Taylor's voice is also a callback in itself, with her imitating the breathy, plaintive tone of her first three albums, which is genius, because she is going back to high school in the lyrics with a surprising and heartbreaking twist.

The story is simple, a variation of Fearless's track six, "You Belong With Me," with the object of her affection a boy who's dating the wrong girl, so she chooses not to kiss him when she had her chance. Later, he's available, but she's worried about the ex-girlfriend ("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 we should"), and so they miss their chance.

We know it's a "Fifteen" song because her legendary BFF Abigail shows up with "the bad news," and we discover that the unkissed boy has passed away after Taylor left to pursue her dreams. I'm choking up with tears just typing the lyric, "But I whispered at the grave / Should've kissed you anyway." 

I wonder what my neighbors think when I'm running and crying at the same time when I listen to this album on my morning run? It's a weird vibe!

Two interesting things happen in this song for me. The music is happy as hell, with a super-catchy melody and the aforementioned backbeat rhythm that gives the song an upbeat vibe. In this sense, it reminds me of the Everclear classic "Wonderful," which sounds like an upbeat alt-rock single, but the lyrics are a teenage boy screaming with rage at his parents' divorce.

In the same way, Taylor's heartbreak at this unexpected loss—a loss of teenage innocence, no less, since they never kissed—juxtaposed against a happy, upbeat musical arrangement only intensifies the emotion of his death and her reaction.

The other thing she does that I love in this song is how she plays with the syllables of the words "invitation" and "convenient" in the chorus. It's hard to reproduce in writing, but she stresses and elongates the "tay" sound in invitation (an-in-vi-TAY-shuun) and stretches out convenient into a triplet (cuuun-veeen-uunt). The way she changes the rhythm of those words makes them sound so interesting.

The final chorus is backtracked with about four levels of background vocals, probably all Taylor herself, but her lead track jumps out with the lesson learned: "My advice is always ruin the friendship / Better that than regret it for all time." The literary allusion is from Tennyson—"Better to have loved, and lost, than never loved at all," from his poem "In Memorium A.H.H.," in which someone he loved also died.

When you survey the brilliance of her former track sixes, it's easy to see why she placed this song at six on Showgirl. While this song will probably not scale the same heights as "22" or "Shake It Off" in terms of worldwide popularity, it's alignment with "You Belong With Me" and "But Daddy I Love Him" will almost certainly elevate this song to a fan favorite. 

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