When Taylor Swift revealed the tracklist for her album The Life of a Showgirl, many fans were particularly intrigued by a song titled Ruin the Friendship.
Though most speculated that the song was about the singer’s rumored falling-out with Blake Lively, they were surprised to learn that it was about something entirely different: Taylor’s hidden love for a high school friend and her regrets about not pursuing that relationship.
Years before she became a global superstar, Taylor and Jeff Lang attended Hendersonville High School in Hendersonville, Tennessee. In November 2010, he tragically passed away at the age of 21.
The mother of Taylor Swift’s late high school friend has reacted to Ruin the Friendship, the song believed to be about her son
Image credits: Erika Goldring / Getty Images
In the emotional song, the Grammy-winning artist recalls being told the news by another high school friend and flying home for Jeff’s funeral. “I whispered at the grave; Should’ve kissed you anyway,” she sings on the track.
Jeff’s mother, Susan Lang, said in an interview with The Tennessean that she was surprised that the superstar hasn’t forgotten about her son “after all this time.”
Image credits: Taylor Swift / YouTube
Susan shared that Taylor and Jeff were “really good friends.” Fifteen years after the tragedy, the mom still keeps a framed photo of her late son standing with Taylor in her home.
“She’s keeping his name alive,” Susan said.
She added that the deep bond Taylor and Jeff shared is “rare” these days. “They hung out at her house a lot. They were always joking around with each other.”
Susan Lang thanked the superstar for “keeping [Jeff’s] name alive” in a new interview
Image credits: taylorswift / Instagram
Though the pop star never names Jeff directly in the song, she references several places where they used to spend time together, including a road in the greater Nashville area and a lake believed to be Old Hickory Lake.
“You drive 85 / Gallatin Road and the lakeside beach / Watching the game from your brother’s Jeep / Your smile, miles wide,” Taylor sings at the beginning of the song.
She reveals that she liked her classmate but didn’t kiss him because he had a girlfriend at the time.
Image credits: alrightnahh18 / X
Then, in the second verse, she recounts going to prom with another date and noticing that Jeff seemed to have feelings for her, too.
“Wilted corsage dangles from my wrist / Over his shoulder, I catch a glimpse/ And see / You lookin’ at me,” she sings. “And it was not / An invitation / But as the 50 Cent song played / Should’ve kissed you anyway.”
She later admits that kissing him wouldn’t have been “convenient,” but it would have been “the best mistake.”
Taylor and Jeff were close friends and went to high school together in Hendersonville, Tennessee
Image credits: BMI / YouTube
Image credits: BangSwift1313 / X
The song then jumps ahead in time to when Jeff broke up with his girlfriend, but Taylor still didn’t make a move because it might have “pissed off” his ex and because “staying friends is safe.”
In the bridge, she reveals that she lost touch with Jeff after high school, until a close friend, Abigail, called her “with the bad news.”
In the song, Taylor reveals a secret crush on a close friend from high school who later passed away
Image credits: Springfield Memorial Gardens
“Goodbye / And we’ll never know why,” she sings, implying that her friend left the world suddenly.
“It was not an invitation / But I flew home anyway / With so much left to say / It was not convenient / But I whispered at the grave / Should’ve kissed you anyway.”
The song concludes with Taylor addressing her listeners directly, advising them to “ruin the friendship” and “answer the question,” because they’ll never know whether they’ll get another chance with the person they love.
Image credits: taylornation / Instagram
In 2010, Jeff was a junior at the University of Tennessee Chattanooga, where he majored in biology, according to The Tennessean and an obituary from the Hendersonville Memory Gardens and Funeral Home.
In the recent interview, Jeff’s mom confirmed that her late son was always the first to hear Taylor’s new songs.
Taylor sings that she should have “ruined the friendship” and kissed her friend before it was too late
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Image credits: Susan Lang / Facebook
On TikTok, a user who claimed to be Jeff’s cousin reacted to a video featuring lyrics from Ruin the Friendship, sharing that his cousin allegedly knew that Taylor “was going to be something incredible.”
Days after the tragedy, Taylor, then a country musician, honored her late friend during her acceptance speech for Country Songwriter of the Year at the 2010 BMI Awards in Nashville.
Jeff passed away in November 2010 at the age of 21
Image credits: Susan Lang / Facebook
Image credits: Taylor Swift / YouTube
“Yesterday, I sang at the funeral of one of my best friends, and he was 21,” she said.
“I used to play my songs for him first. So I would like to thank Jeff Lang and as always, all the creative minds in this room who inspire me every day.”
Listen to Ruin The Friendship below
Fans believe Taylor has written another song about Jeff: the vault track Forever Winter (Taylor’s Version), released in 2021 on the re-recorded version of her album Red.
In the song, the 35-year-old sings that “all this time” she didn’t know that someone she knew was “breaking down.”
She also sings, “I’d fall to pieces on the floor / If you weren’t around / Too young to know it gets better.”
Many fans said that they cried while listening to Ruin The Friendship 
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