If you’ve been on the internet at all today, you’ve likely seen that Taylor Swift has officially released her 10th studio album, Midnights.
The album is, by Taylor’s own admission, a “wild ride” of “highs and lows and ebbs and flows” — and things were only made more chaotic with the subsequent release of Midnights (3am Edition), an additional album containing 7 extra songs, which dropped just 3 hours after Midnights did.
Between all 20 songs in total, Taylor most certainly upholds her ~reputation~ of nodding toward other celebrities in her lyrics, with Midnights seemingly charting several past breakups, feuds, and so much more.
One track in particular that has garnered huge attention online is “Would’ve, Could’ve, Should’ve,” which is on Midnights (3am Edition).
Given that the song is explicitly about “regret,” and that Taylor makes several references toward age-gaps in relationships throughout, fans have theorized that “Would’ve, Could’ve, Should’ve” is a reflection on the older men that she dated in the past.
For a bit of background, Taylor infamously dated John Mayer back when she was 19, and he was 32. Less than a year after reports claimed that they’d split, Taylor all but confirmed the breakup with the release of a very pointed song on her 2010 album, Speak Now.
Aside from literally titling the track “Dear John,” Taylor sang the lyrics: “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.”
John has long faced scrutiny for the 13-year age gap between himself and Taylor. He was even questioned about her lyric, “Don’t you think I was too young to be messed with?” during a past interview, though quickly shut the subject down, saying he didn’t “want to go into that.”
Shortly after John, Taylor was romantically linked to actor Jake Gyllenhaal, when she was 20 and he was 29. According to reports, their relationship ended after a brief few months, with a source telling Us Weekly at the time that Jake “wasn’t feeling it anymore.”
Taylor’s famous song “All Too Well” — which was originally released the year after her apparent split from Jake — seemingly charts their rocky past relationship, with a notable reference toward a stark age difference between two lovers. “You said if we had been closer in age maybe it would have been fine / And that made me want to die,” she sings in the full 10 minute version, released last year.
So, with all this in mind, let’s delve into the lyrics on “Would’ve, Could’ve, Should’ve” — which fans are calling “the darkest song Taylor has ever written.”
Would’ve, Could’ve, Should’ve is the darkest song Taylor has ever written. I’m literally nauseous, it was grooming point blank. And Taylor called him out on it
From the very first verse, Taylor immediately references a “grown man” who she was once romantically involved with, while she was, in her own words, “a child.” She sings, “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?”
In light of everything we’ve discussed about Taylor’s past relationships, fans were quickly left wondering whether these lyrics were perhaps in reference to John or Jake.
not now babe I’m trying to figure out if Taylor wrote would’ve, could’ve, should’ve about Jake or John https://t.co/sNjoKY5aB6
Some people were initially swayed by the idea that Jake is the subject of the track, suggesting that Taylor was later singing about regretting the fact that he was the first person she had sex with — a long-swirling rumor that has never officially been confirmed.
Just last month, in fact, Taylor all but confirmed a years-long theory that the “scarf” she mentions in “All Too Well” — which she says she left at her lover’s sister’s house — was a metaphor for the fact she hadn’t had sex. Several fans took this into account when decoding the lyrics on “Would’ve, Could’ve, Should’ve.”
Taylor sings: “If you never touched me, I would’ve gone along with the righteous / If I never blushed, then they could’ve never whispered about this.”
“And 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,” she goes on.
One fan theorized, “idk maybe should’ve could’ve would’ve is about jake purely based on Taylor confirming the scarf metaphor at the film festival and like the metaphor was a nice was for her to explain but now she’s like ‘real shit: that sucked.’”
idk maybe should’ve could’ve would’ve is about jake purely based on Taylor confirming the scarf metaphor at the film festival and like the metaphor was a nice was for her to explain but now she’s like “real shit: that sucked”
However, given that Taylor goes on to specifically mention the age she was when she dated the mysterious “grown man” in question, it seems more plausible that she’s perhaps referring to John rather than Jake.
As mentioned, Taylor was 19 when she dated John, then-32. On the Midnights track, she sings: “I damn sure would’ve never danced with the devil at 19.”
As one Twitter user summarized, “Taylor and Jake did not even meet and start dating til the Fall of 2010 when Taylor was months away from her 21st birthday (even referred to it in ATW).” As we know, things with Taylor are never just coincidental, and it seems interesting that she mentioned the specific age of “19” in this song.
@justincferrell Did you even listen to the chorus?”And I’m damned sure I never would’ve danced with the devil at 19″—Taylor did not even meet Jake Gyllenhaal til the fall of 2010 months before her 21st birthday.When she was 19 she was dating John Mayer.
Taylor then goes on to express “regret” at the past relationship in question, suggesting that she’s grown aware of how problematic it was since getting older. “And now that I’m grown, I’m scared of ghosts / Memories feel like weapons,” she sings.
“God rest my soul / I miss who I used to be… I regret you all the time / I can’t let this go, I fight with you in my sleep,” she continues. “The wound won’t close / I keep on waiting for a sign / I regret you all the time.”
And, perhaps most poignantly, Taylor then pleas for her “girlhood” back — a lyric that left fans devastated. “Give me back my girlhood, it was mine first,” she sings.
“no but ‘give me back my girlhood, it was mine first’ is one of the saddest lyrics taylor swift has ever written :(” one person tweeted.
no but “give me me back my girlhood, it was mine first” is one of the saddest lyrics taylor swift has ever written 🙁
“‘give me back my girlhood it was my first’ is the most heartbreaking taylor swift lyric i’ve ever heard,” echoed another.
“give me back my girlhood it was my first” is the most heartbreaking taylor swift lyric i’ve ever heard
What’s more, as “Would’ve, Could’ve, Should’ve” comes to an end, the next song on the tracklist is, perhaps conveniently, a track called “Dear Reader,” which several fans immediately tied to her aforementioned breakup hit, “Dear John.”
“putting a song called ‘DEAR reader’ after a song that absolutely annihilated mr. dear john was so intentional,” one person suggested, while others highlighted the “parallels” between both titles. In fact, some people went so far as to label “Would’ve, Could’ve, Should’ve” the darker version of “Dear John,” or “Dear John 2.0.”
putting a song called “DEAR reader” after a song that absolutely annihilated mr. dear john was so intentional #TSmidnighTS
“Give me back my girlhood It was my first… And I damn sure wouldn’t have danced with the devil at nineteen” would’ve could’ve should’ve is Dear John 2.0 #TSmidnighTS
All in all, fans are heartbroken for Taylor after listening to her apparent regret at the past relationship, suggesting that she’d been calling the subject in question out for “grooming” her. You can listen to “Would’ve, Could’ve, Should’ve,” and the whole of Midnights, here.
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