Would’ve, Could’ve, Should’ve

In 2009, 32 year old singer John Mayer was rumored to be romantically involved with then, 19 year old Taylor Swift after the two collaborated on Mayer’s, “Half of My Heart” together. A few months later, it became clear a split had taken place, especially after Swift’s 2010 album Speak Now included a biting break-up track, titled “Dear, John.” Seemingly confirming both the relationship and the break up, Swift vividly depicted the volatility of their short-lived romance and the regret she had looking back on all of the warnings she ignored about Mayer and their relationship in her spin on a “Dear, John letter.” In the decade-plus following the release of the album, Mayer made it incredibly clear there was no love lost between him and Swift, even remarking that the track was “cheap songwriting” in a Rolling Stone interview.

With Swift now 32 herself, it was unsurprising to many fans when she revisited this previous relationship, ripe with power imbalances, in her newest album Midnights. “Would’ve, Could’ve, Should’ve” is a scathing sequel to “Dear John” made even more poignant with the powerful insight Swift now has on just how inappropriate their relationship truly was. It is a relationship that keeps her up at night, to this day, 12 years later; desperately longing for the girl she used to be, before she was corrupted by Mayer.

Swift writes in the first stanza:

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?

This lyric is the perfect opening to the song, establishing the reality of just how many eyes were on their relationship at the time. Swift had notoriously been a target for the media’s slut-shaming, and her relationship with Mayer was no exception. Despite the fact that she was the younger, less successful, less powerful and less wealthy of the two, she was still criticized for her role in their relationship. She was seen as the one tainting his “promising” reputation, or splattering paint on him as it were, when in reality he was the one crossing lines as the true adult in the relationship. She establishes the imbalance further, stating outright that she was nothing more than a “child” during their romance, while he was a “grown man.” Furthermore, she references the saying “washing your hands of someone” to show just how much Mayer wanted to forget about their relationship after it ended. He wanted to wash the paint she splattered on him away, and he can. He erases her from his life just as easily as he could get paint of his skin. For Taylor, it’s not that easy, though. What was just a few months for him, is something she can never escape. What he did to her haunts her everyday:

I regret you all the time

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

There is a clear sense of desperation to these lyrics. The lingering emotions and damage from their relationship spill out into every aspect of Swift’s life. Even in her unconscious mind she is thinking about him, longing for closure. Like a wound that keeps getting opened up again and again. She can’t escape the effects of the cut, no matter how long ago it happened, it is too deep and permanently changes and disfigures her. She regrets him in her conscious moments as well, so deeply, in fact, that shes looking to a higher power with her pleas for closure.The sign she’s looking for is a reference to a sort of bargaining with god to restore her to the innocent child she once was before she was touched by Mayer. The song is filled with religious illusions depicted in the lines above and below in order to portray the innocence that Swift was robbed of as a result of their relationship:

I would’ve stayed on my knees

And I damn sure never would’ve danced with the devil

At nineteen

This relationship was Swift’s fall from grace. She depicts her self, devoted in prayer, or staying on her knees, as a way to represent the purity of her life before Mayer. She states that “all I used to do was pray” and without the influence of Mayer, or the devil as she not so subtly portrays him, she would’ve “gone along with the righteous.” She was on the path of virtue and innocence, before she was lured in to the hands of the devil. He was the one who took her away from “god” and “innocence” and changed her. She wishes she could go back to them simplicity of before she was taken advantage of.

Mayer was incredibly alluring, and in many interviews Swift remarks how excited she was to be working with Mayer because she was such a big fan of his. She writes:

If you never saved me from boredom

I could’ve gone on as I was

But, lord, you made me feel important

And then you tried to erase us

Oh, you’re a crisis of my faith

Mayer was able to slip into her life offering excitement, praying on her naivete at just 19 years old. Her “crisis” was her youth and her belief in Mayer and his words: making her feel loved and important in ways she had never felt because of her youth. He groomed her, much like the saying “idle hands make the devil’s work,” Mayer took her into his world and corrupted her, irrevocably changing her. Then a few months later he decides he doesn’t want anything to do with her anymore so he erases her from his life, easily, like he washed the paint of his hands earlier.

The most heartbreaking line of the song is when Swift finally ends the bridge the song had been building to:

Living for the thrill of hitting you where it hurts

Give me back my girlhood, it was mine first

This is just the nail in the coffin for Mayer. It is a true highlight of just how young Swift was when she experienced this trauma. The lines are incredibly childish, the first one reading like an eye for an eye almost: he hurt her so she wants to hurt him back. Now, she finally sees just how wrong what happened was, and in a childlike way she wants to get back at him even though in her current perspective as an adult she knows she can’t. The following line clinches the absolute heartbreak of the song. The “it was mine first” plays a dual role in again highlighting the childlike nature of her 19 year old self, perfectly encapsulating the gap of maturity in the relationship but also revealing just how much Mayer stole from her. Their relationship ripped her out of her childhood and she can’t forget it that so easily like Mayer can.

7 thoughts on “Would’ve, Could’ve, Should’ve


    I really like this analysis as it is unique and such a fresh take on this very new song. I’ve never thought of the lyrics in this way, specifically Swift illudes to her prior innocence and purity.


  2. Grace H.

    I think this is a really powerful analysis. I love the emphasis you put o the splattered paint analogy, as it really shows how easily John was able to erase the effects Taylor had on his life. While I knew of this imbalanced power dynamic, your analysis truly solidified its haunting effects on Swift.


    1. Cimya L.

      Wow, I never really knew the essence of this Taylor Swift song, but your analysis of it really brings a good argument to the way this musical poem is a poem. The words of the lyrics shown were really deep beyond my knowledge. And you just did a really good job of explaining the meaning of the song.


  3. Khylie A.

    I really like your analysis of this piece, I feel you bring a good argument in defense of this piece being a poem. The way you articulated your ideas really deepened and expanded my understanding of this piece.


  4. Annika C.

    I agree with the argument you made and think you have a strong analysis here. I haven’t really thought about the meaning of this song much, but I definitely agree with your point about her loss of innocence.


  5. Meredith M.

    This is an excellent analysis. You really captured the song and its deeper meaning. I really appreciate the context you supplied at the beginning. This song is one of my favorites she’s ever written, and I think it is truly heartbreaking. It is so desperate and written from a much more mature perspective and you really explained it so well.


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