[Warning: Potentially Triggering Content]
The story behind Ruin The Friendship is so heartbreaking.
If you’re anything like us, you were jamming to The Life of a Showgirl when track 6 started playing and brought an unexpected tear to your eye! The track is all about falling in love with a classmate at the wrong time — cause he’s got a girlfriend. Taylor sings about wishing she would’ve kissed the boy after a game and at prom, but it “was not convenient” and she didn’t get an “invitation” to do so.
Related: Did Taylor Swift Take Another Jab At Charli XCX?
Flash forward, she gets a call from her friend Abigail Anderson Berard with devastating news:
“When I left school, I lost track of you / Abigail called me with the bad news / Goodbye, and we’ll never know why / But I flew home anyway / With so much left to say / It was not convenient / But I whispered at the grave / ‘Should have kissed you anyway.’”
Having learned about regrets the hard way, Tay shares some advice with her fans to conclude the song, urging:
“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.”
Take a listen:
So, who is this mystery guy, and what happened? It appears to be about her childhood friend, Jeff Lang, who sadly died in 2010 after a battle with addiction and depression, per reports. He was just 21.
According to the Chattanooga Times Free Press, he died “from an inflammation of the lungs called acute bronchopneumonia, according to a separate medical examiner’s report,” and “Methadone was a probable contributing factor in Lang’s death.” Methadone is often used to treat opioid dependence, such as by relieving withdrawal symptoms and reducing cravings.
The BFFs can be seen together (below):
She must’ve really, really loved him to still be harboring regret and wondering what could’ve been two decades later pic.twitter.com/F0AzBG5HvO
— ivs
???? (@flanneIcure) October 3, 2025
Taylor flew home at the time to attend his funeral, tearfully sharing that same week while accepting the Country Songwriter of the Year Award at the BMI Country Awards:
“It’s been a really emotional week for me. … Yesterday, I sang at the funeral of one of my best friends. He was 21, and I used to play my songs for him first. So, I would like to thank Jeff Lang.”
Fans have speculated her songs Forever Winter and Bigger Than the Whole Sky are also about Jeff. So sad. It was clearly a very painful and impactful loss for Taylor. What a beautiful message she was able to impart with the song, though.
R.I.P., Jeff…
If you or someone you know is experiencing substance abuse, help is available. Consider checking out the resources SAMHSA provides at https://www.samhsa.gov/find-help/national-helpline or check out StartYourRecovery.org.
If you or someone you know is contemplating suicide, help is available. Consider contacting the 988 Suicide & Crisis Lifeline at 988, by calling, texting, or chatting, or go to 988lifeline.org.
For resources on mental health, visit https://www.nimh.nih.gov/health/find-help.
[Image via Netflix/YouTube & Springfield Memorial Gardens]
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