Taylor Swift’s Brutal John Mayer Diss Track Has Fans Shook: Her ‘Darkest Song’ Ever

Taylor Swift broke the internet—and Spotify—when she released her highly anticipated tenth studio album Midnights on Friday, Oct. 21. And over the last 24 hours, fans have spent every moment dissecting each track as they hunt for Easter eggs to gain more insight into the woman behind the mic.

And because she is Taylor Swift, she couldn’t help but drop a few more surprises along the way.

One such surprise was an extended edition of Midnights, featuring seven extra songs that she dubbed “the 3AM tracks.”

But there is one track in particular from the extended Midnights (3AM Edition) that has fans talking, and that is “Would’ve, Could’ve, Should’ve,” which is deliberately placed as track 19 on the album (more on why that matters so much in a moment).

It is easy to understand why the song has fans fired up. It seems to directly reference Swift’s tumultuous relationship with fellow singer John Mayer, who dated her when he was 32 and she was 19. So it’s fair to assume that this song being the 19th track on the album is not a coincidence—especially knowing Swift and her penchant for Easter eggs.

The two singers dated briefly between 2009 and 2010. When they broke up, Swift released “Dear John,” which was one of the only times she directly addressed what went down in their relationship. Besides the obvious fact that she named the track after him, there are lyrics that reference, among other things, their 13-year age gap: “Don’t you think nineteen is too young? / To be played by your dark twisted games when I loved you so? / I should’ve known.”

But when you listen to “Would’ve, Could’ve, Should’ve”, “Dear John” seems like a cute little lullaby in comparison.

This song is the grown up, mature version of the Speak Now track from 2010. The emotions aren’t so raw anymore. Swift has evolved, and so have her feelings. She’s had time to process and really understand what her relationship with the singer was like. But that doesn’t mean it hurts or confuses her any less. The resulting lyrics are scathing, to say the least—so much so that fans have dubbed this the darkest song the singer has ever written.

In the very first verse, Taylor references a “grown man” who was involved with, by her own admission, “a child.”

“If you tasted poison you could've spit me out at the first chance / And if I was some paint, did it splatter on a promising grown man? / And if I was a child did it matter if you got to wash your hands?,” she sings.

At first, this may seem like a reference to her relationship with actor Jake Gyllenhaal, another ex of Swift’s, who is nine years older than the singer. However, it becomes clear she’s talking about Mayer when she references her age directly in the song.

“And I damn sure would’ve never danced with the devil at 19 / And the God’s honest truth is that the pain was heaven / And now that I’m grown, I’m scared of ghosts / Memories feel like weapons, and now that I know, I wish you left me wondering,” she sings on “Would’ve, Could’ve, Should’ve.”

(As fans may recall, Swift and Gyllenhaal dated when the singer was 20, as referenced in her song “All Too Well” from her third album Red.)

Swift then talks about just how traumatic that experience was, singing that she “regrets” it all the time. The thoughts of this failed relationship keep her awake at night because she still can’t seem to let go of it after all these years.

But perhaps the most poignant moment in the entire song is during the bridge, when she pleads for her “girlhood” to be returned to her.

“Give me back my girlhood, it was mine first,” she sings. This is the lyric that has left fans absolutely devastated.

This moment strikes a chord with people because it can happen to any of us—even a superstar like Taylor Swift. Many people can relate to being in a relationship that they probably shouldn’t have been in when they were too young to know better. The pain of leaving a situation that you only later realize was incredibly toxic, when you get the chance to sit with it for a while, is familiar. There’s the regret of being a part of it in the first place. Of devoting so much time, effort, and energy—only to never have it reciprocated.

“Would’ve, Could’ve, Should’ve” is Taylor Swift reflecting on her relationship with Mayer from her enlightened vantage point as an adult. It also serves as an apology to herself for letting him into her life at the age that she did, knowing things would’ve been very different if she hadn’t.

Midnights is the singer at her most vulnerable, and “Would’ve Could’ve Should’ve” is probably her darkest foray into that emotional space yet. It is a clear indication that Swift has grown up, and we’ve all grown up along with her. She’s had time to sit with her emotions, and now she’s channeled them into her most haunting song yet. And if nothing else, one thing is very clear: Taylor Swift isn’t holding back. Not anymore.

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