Taylor Swift, Olivia Rodrigo & the Sexist Pitfalls of ‘Confessional’ Songwriting

On October 21st, Taylor Swift dropped her 10th studio album, Midnights and, 3 hours later, released the deluxe 3am version with seven bonus tracks. Out of the seven, the penultimate track “Would’ve Could’ve Should’ve” became an immediate fan favorite. The song, which appears to be inspired by her relationship with John Mayer, seemingly explores Swift’s regret about getting involved with him, stating, “I can’t let this go/I fight with you in my sleep/The wound won’t close/I keep on waiting for a sign/I regret you all the time”. 

Much like Speak Now’s “Dear John”, “Would’ve Could’ve Should’ve” notes their 13 year age gap when Taylor was 19 and John was 32. Now 32 herself, Swift’s lyrics explore how, despite the 13 years that have passed, she is still reeling from the aftermath of the relationship and her inability to move on from the trauma experienced during the partnership. 

Naturally, fans immediately picked up on the connection between the two songs and it became a trending topic on Twitter shortly after its release. I even tweeted a joke about John Mayer paying for his crimes again and the pushback I received was alarming. Many replied with the same tired criticism of Taylor — that she only writes about her failed relationships and that she can’t keep a man so she should look in the mirror. What was unnerving was the critiques that Swift should no longer be writing about it because it happened so long ago. 

For years, music has been used to express and process trauma. After the September 11 attacks in 2001, music therapists provided music-related activities — songwriting, singing, and listening to music — to reduce stress and process the trauma associated with the tragedy. In relation to singer-songwriters in the music industry, songwriting helps the artist regain the agency to tell their own stories by safely reflecting on the experiences. 

It raises two questions: who is allowed to make music about their emotions and experiences and is there a time limit on when they should just “get over it”?

Artists like Drake, Justin Bieber, Ed Sheeran, and the like have notoriously written about their relationships, successful or not. Those aforementioned artists are praised for their songwriting while female songwriters are labelled as “confessional.” During the album cycle for 1989, Swift brought up the double standards female songwriters face, telling the Australian radio show Jules, Merrick & Sophie, “that’s a very sexist angle to take. No one says that about Ed Sheeran. No one says that about Bruno Mars. They’re all writing songs about their exes, their current girlfriends, their love life, and no one raises the red flag there.” 

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