Taylor Swift being nostalgic about a high school crush was not on the Showgirl bingo card for “Ruin the Friendship”, especially when she’s being pulled into a legal battle between bestie Blake Lively and Justin Baldoni. However, it was a delightful but heartbreaking surprise to hear that Swift wrote a third song seemingly about her late high school friend, Jeff Lang. While she doesn’t specifically mention Lang during her insights into the song, she does give us plenty of hints that the muse might be the same as “Bigger Than The Whole Sky” and “Forever Winter.” “‘Ruin the Friendship’ is a song that wistfully goes back in time to moments that you hesitated, moments that you were too scared or anxious to do something that you were really curious about,” Swift shared through Amazon Music. “The idea of if you told this person you have feelings for them, or if you kiss this person, you might ruin the friendship.”
Throughout the song, Swift reminisces about her teenage years in Hendersonville, Tennessee, making references to spots in her hometown, such as “Gallatin Road and the Lakeside Beach,” as well as her time at prom while a “50 Cent song played.” She doesn’t need to tell us it was “Candy Shop” — the Showgirl went to prom several times, including in 2005 when 50 Cent was everywhere. 50 Cent, himself, was honored to be on the track. “@taylorswift13 shit is popping right now, she shout me out, she don’t shout you out. LOL THIS IS FOR BIG TIMERS ONLY! wait I’m the only shout out on the whole album,” he wrote on X, possibly not realizing that the song is about her friend dying.
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Abigail Anderson, who was the inspiration behind “Fifteen” and Swift’s best friend from high school, gets a shout-out in the most devastating verse of the song: “When I left school, I lost track of you/Abigail called me with the bad news/Goodbye/And we’ll never know why.” Lang died in November 2010, just a week after Speak Now was released. Swift honored her late friend as she accepted the award for Songwriter of the Year at the 2010 BMI Country Awards. “It’s been a really emotional week for me,” Swift tearfully began in her speech. “Yesterday, I sang at the funeral for one of my best friends, and he was 21. I used to play my songs for him first, so I would like to thank Jeff Lang.”
In the original “Forever Winter” demo from 2012, two years after Lang’s death, Swift hints that she had feelings for Lang in the final line; she ended up changing it for the vault track. She originally sings, “He says, ‘Why fall in love’/I say, ’‘cause I won’t go away.’” The singer re-recorded the song sometime in 2021 for Red (TV), possibly around the same time she started working on Midnights, which included “Bigger than the Whole Sky” in the 3 a.m. Edition. It’s not out of the question for Swift to be nostalgic for an unrealized crush, or even just a late best friend she wishes she could invite to her wedding. The Life of a Showgirl needed a crying song, and this was it.
