“Ruin The Friendship” is a new song from Taylor Swift’s twelfth studio album, The Life of a Showgirl. This song is a standout track from the album–sonically, conceptually, and lyrically beautiful and revealing. This song contains some of the best storytelling on the album. This song combines sonically whimsical, pop, and light country elements, which makes sense as it relives an experience that has carried over from high school. Taylor Swift started her career in high school, making country music, which transitioned to country-pop, which transitioned to full-blown pop, which transitioned to indie/folk, which transitioned back to pop. You can say a lot about Taylor Swift, but you can’t say that she’s not one of the most prolific artists of today…or of all time, honestly.

These melodies are infectious, the production connects with the story, and the storytelling is the most prominent and crucial aspect of this song.

This track six broke the mold from her previous albums, where usually, she would hit emotionally hard with the vulnerability of track five and pick us back up during track six. And at first listen, you’d think that was what happened. However, the plot twist in the third verse of this song shocked her audience. And this song is one of the most essential tracks on this album and in her discography.

For context, this song is clearly about the same subject that “Forever Winter” is about. She was friends with this guy in high school, Jeff Lang, and unfortunately, he passed away at 21 by ending his own life. He evidently struggled with mental health and substance abuse issues. We knew they were close friends, and that death impacted her, but what we didn’t have confirmation of until now is that she was romantically interested in Jeff, and she never got the chance to tell him how she felt or take action to show him that. It’s a song about taking chances before they become regrets. “My advice is always ruin the friendship, better that than to regret it for all time (Should’ve kissed you anyway). My advice is always answer the question, better that than to ask it all your life (Should’ve kissed you anyway).”

Let’s break down the lyrics:

VERSE 1:

“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.”

The beginning of the song immediately sets the scene, painting a clear, precise picture. We know exactly when and where this takes place — early fall in Hendersonville, TN. Gallatin Road is a main road in Hendersonville, TN.

The subject of the song is driving on the road at 85 MPH. She’s setting the scene with a dreamy soundscape and vivid imagery.

CHORUS 1:

“And it was not an invitation

Should’ve kissed you anyway

And it was not convenient, no

But your girlfriend was away

Should’ve kissed you anyway”

She’s basically saying that there was never a good time for her to make her move. She’s saying that she wishes she had shot her shot, even though it was never “convenient.” I don’t condone cheating, but I don’t think that’s the point of this lyric. It’s merely about the theme of regret, which we’ll get to.

VERSE 2:

“Shiny wood floors underneath my feet

Disco ball makes everything look cheap

Have fun, it’s prom

Wilted corsage dangles from my wrist

Over this shoulder, I catch a glimpse

And see…You looking at me.”

CHORUS 2:

“And it was not an invitation

But as the 50 Cent song played

Should’ve kissed you anyway

And it was not convenient, no

Would’ve been the best mistake

Should’ve kissed you anyway”

This provides further confirmation that this experience happened in high school (“it’s prom”). And the 50 Cent reference brings us right back to this time.

The lyric “Disco ball makes everything look cheap” could potentially connect to the song “mirrorball” from folklore. folklore, which is my favorite album of all time, did some irreparable damage to her career. It’s almost universally considered to be her best album; however, it’s all people expect from her now. Every subsequent album has been compared to it, which I don’t think is fair. Therefore, every album that came after folklore has looked “cheap,” because…it’s not folklore. I’ve also seen people trying to give her ex, Joe Alwyn, more credit for folklore and its sister album, evermore, than he deserves. She is the songwriter and storyteller of her music. She has collaborators who assist her with production and editing, but these are her thoughts, feelings, words, and ideas, and nobody else can take credit for that.

BRIDGE:
“Don’t make it awkward in second period

Might piss your ex, maybe 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, maybe we’ve been good, staying friends is safe, doesn’t mean you should.”

Many people remember the feeling of being in high school, sitting in class, trying not to feel or seem awkward because there’s a person there who you’re romantically interested in, and you don’t know how they feel. This bridge subtly reveals the theme of the song before it’s explicitly stated at the end of the song (“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”

This is when things start to shift, and you start to realize the true meaning of this song.

CHORUS 3:

“It was not an invitation

But I flew home anyway

With so much left to say

And 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 —”

POST-CHORUS:

“My advice is always ruin the friendship, better that than regret it for all time

My advice is always answer the question, better that than to ask it all your life

Should’ve kissed you anyway”

OUTRO:

“Should’ve kissed you anyway.”

She repeats “should’ve kissed you anyway” so many times to convey how deeply she regrets not taking this chance. The post-chorus at the end here represents the thesis statement of this song, which is: Don’t live your life with regret. Take chances before they become regrets. The reality of the world is that you have to look out for yourself because no one else will. Sometimes we make sacrifices to better ourselves or our careers or our relationships, and then other aspects of our lives get overshadowed or neglected.

This song is so important to the album and in general because…

It tells a story of something she thought about behind the scenes, which is on theme for this album.

This story has a subtextual theme of “I’m living the life of a showgirl; therefore, I miss out on important personal events and relationships.” “Now I know the life of a showgirl, babe, and I’ll never know another.”

This song also likely explains her past relationship patterns. There’s this notion that Taylor Swift doesn’t like to be single or alone, and as soon as she ends a relationship, she enters a new one, and I personally think this song tells us that this situation with Jeff was a catalyst for her mentality to shift, and she’s taken advantage of just about every opportunity she’s been able to, because that feeling of regret and “what could’ve been” within this relationship haunts and impacts her. Losing a close friend, who you had feelings for and never got a chance to act on them or communicate them, is something that I don’t believe you ever truly get over or move past. You can cope with and manage the grief, but it never really goes away.

As someone who has attempted to end my life many times, mostly as a teenager, this song is also important to me because it provides an alternate perspective for me. It showcases how this choice can have lasting impacts on the people around you, whether you realize how profoundly you’ve left your mark on the world or not. And often, people who commit suicide are not aware of their impact, because their mind is clouded with cynicism and hopelessness. Believe me, I would know.

She wrote Jeff one last song before she gets married to Travis, and that thought makes me really emotional. Yes, it’s a tad parasocial, but frankly, I don’t care. I’m so ecstatic for my close, personal friend, Taylor Swift. But truly, this kind of experience never, ever leaves you. I also believe that genuinely falling in love with your person–the person you know you’ll spend your life with–brings up past memories about regrets and relationships that have gone unprocessed or unaddressed. I’ve been there. I met my partner four and a half years ago, and I’m still trying to process the trauma I’ve endured from men and, in general, from my past.

I believe it’s completely uncalled for and invalid to say something like, “She’s 35–why is she still writing about high school?” or “She’s capitalizing on her friend’s death.” Do you realize how tone-deaf and disrespectful that comes across? Just because she’s Taylor Swift, the most famous person in the world, does not mean she deserves these hateful opinions thrown around. She’s not immune to criticism–nobody is. However, there is a difference between constructive criticism and full-blown hatred or deliberately missing the point.

This song also showcases much of Taylor’s unprocessed grief and guilt around this situation and the lasting impacts it’s had on her throughout the rest of her life. As I said, this song certainly provides an eye-opening perspective on Taylor’s relationship patterns, including seeking different parts of Jeff in her exes. Jeff was the one guy she never had and couldn’t save.

Remember to check out all of my social media and stream The Life of a Showgirl!

Check out my TLOAS reaction and breaking down the whole album on my YouTube channel!