Raw Regret: Taylor’s “Would’ve, Could’ve, Should’ve” Meaning, Line by Line
Track 19 on Taylor Swift’s album Midnights turns back the clock to age 19. She describes a romance that scarred her for life, and yearns to time travel and reverse the damage.
What is the central relationship she describes in the lyrics, and why does she regret it so deeply?
Here’s my complete English teacher analysis of Taylor’s Would’ve, Could’ve, Should’ve meaning, line by line.
Would’ve, Could’ve, Should’ve by Taylor Swift
- Title: Would’ve, Could’ve, Should’ve
- Written by: Taylor Swift, Aaron Dessner
- Track: 19, Midnights
- Pen: Quill
- Lyrics from Genius
Would’ve, Could’ve, Should’ve Analysis: Narrative Summary
- Setting: Looking back on a traumatizing relationship.
- Characters: Narrator (Taylor), subject (older man, “you”)
- Mood: Angry, regretful, confused.
- Conflict: He took advantage of her and stole her innocence.
- Inciting Incident: “Danced with the devil”: entered a relationship with a power imbalance.
- Quest: Find parts of herself that she lost, figure out why it happened and what it means now.
- Symbols & Metaphors: “Would’ve, Could’ve, Should’ve,” “blinked,” “first glance,” “poison,” “spit me out,” “paint,” “promising grown man,” “wash your hands,” religious overtones (“pray,” “crisis of faith,” “God’s honest truth”, et al), “on my knees,” “danced with the devil,” “ghosts,” “weapons,” “now that I know,” “touched,” “blushed,” “boredom,””erase us,” “played it safe,” “God rest my soul,” “tomb won’t close,” “stained glass windows,” “wound,” “sign,” “death” & “die,” “tearing down our banners,” “hitting you where it hurts,” “girlhood.”
- Lesson: Sometimes trauma never goes away, and you’ll never fully comprehend what happened.
What is Would’ve, Could’ve, Should’ve About?
This track is about regret, and describes a relationship in Taylor’s teen years that was traumatic. She describes how an older man took advantage of and ruined her, and how she wishes she could go back and make different choices.
Taylor uses religious overtones and metaphors to describe how this relationship damaged her innocence.
Who is Would’ve, Could’ve, Should’ve About?
Taylor has never revealed explicitly who this song is about, but most fans think it describes her past relationship with John Mayer.
Mayer was 32 and Taylor was 19 when they dated, which was shocking to most people: the age gap was large, and there would have been a large power imbalance.
Taylor wrote about their relationship in the song Dear John, and Would’ve, Could’ve, Should’ve has many lyrical parallels to that earlier track.
Would’ve, Could’ve, Should’ve Lyrics Meaning: Line by Line
The first verse looks back on how the central relationship began, and wonders if one tiny thing would have been different if it would have never happened in the first place.
“If you would’ve blinked, then I would’ve / Looked away at the first glance,” she says. If he had only fluttered his eyelids for a millisecond, would their eyes not have met? Would it have caused a butterfly effect (like she also alludes to in Bigger Than The Whole Sky), and changed her future?
“If you tasted poison, you could’ve / Spit me out at the first chance” alludes to Snow White and the poison apple. If he had a hint of how damaging this relationship would be, would he have rejected it from the beginning?
“And if I was some paint”, she wonders, ‘”did it splatter / On a promising grown man?” Did she permanently mark him and damage his reputation as a “promising grown man”?
This alludes to the phrase “promising young woman,” which is also a film by Emerald Fennell. Taylor twists the phrase to describe how this man wasn’t young at all – he was fully grown, and should have been more mature. Did she ruin his future, or did he ruin hers?
“And if I was a child, did it matter,” she wonders, “If you got to wash your hands?” She was too young, and was taken advantage of by him. But did that matter to him when he never had to deal with the fallout?
Did he even care about how much trauma he caused, because he never had to face any consequences?
1st Pre-Chorus & Chorus: “Damn Sure Never Would Have Danced With the Devil”
“Ooh, all I used to do was pray,” she says, describing her former “good girl faith.” This both metaphorically describes her innocence at age 19, as well as her reputation at the time that they dated. She was a young country artist with Christian undertones.
She used to pray “would’ve, could’ve, should’ve,” meaning she used to pray for things to turn out differently. Did her prayers come to fruition? Or did her prayers materialize “the devil”?
“If you’d never looked my way,” she says, “I would’ve stayed on my knees.” If he’d never entered her life, she would still be that “good girl,” and her innocence would still be intact.
If that first glance had never happened, “I damn sure never would’ve danced with the devil / at nineteen.” This both portrays him as the devil, and describes the dangerous game she fell prey to. She was too young and too impressionable, and his devilish charm took advantage of that.
“And the God’s honest truth,” she says candidly, “is that the pain was heaven.” Part of her enjoyed this ‘dance with the devil.’ She got a taste of the forbidden fruit, like Eve in the Garden of Eden, but was punished for it.
“And now that I’m grown, I’m scared of ghosts,” she says, “Memories feel like weapons.” Her memories of him haunt her like a ghost, and she’s afraid of it. Just recalling their relationship still feels sharp and painful.
But this also alludes to memories as something that can hurt him. Does she have secrets about him that could be weaponized?
🌌 Are you a Mastermind? Try my Midnights Lyrics Quiz! 🌌
“And now that I know,” she says, describing what “would’ve, could’ve, should’ve” been, “I wish you’d left me wondering. Looking back on this relationship in hindsight, it’s all clear: he shouldn’t have taken advantage of her.
She fell victim to him, and although it was tempting and alluring to not know how it would end, she wishes she could turn back the clock and avoid him altogether.
Not knowing what could have been is safer than knowing exactly how it ends.
Verse 2: “I Would’ve Gone Along With the Righteous”
The second verse asks more hypothetical questions.
“If you never touched me, I would’ve / Gone along with the righteous,” she says. He has the opposite of a Midas touch: his touch stole her piousness. He took away her “good girl” image, and stole her faith.
“If I never blushed,” she says, alluding to Maroon and a Scarlet ‘A’, “then they could’ve / Never whispered about this.” If she hadn’t fallen for his flattery, she never would have been marked with the Scarlet Letter. Her reputation would have gone undamaged, and the toxic gossip never would have circulated.
What’s ironic is that he is the one whose reputation should have been scarred. But since she’s a woman, she took the blame. Today if a 32 year old celebrity dated a 19 year-old, the gossip would have a very different tone. But then, Taylor was marked as a slut for being involved with him.
“And if you never saved me from boredom,” she says, “I could’ve gone on as I was.” She’s not saying she was bored: she’s saying her world was quieter and not full of the gossip described in the previous lines.
Her life went from relatively “boring” to full-blown tabloid fodder. If he’d never entered her life, maybe she never would have entered the world of media scrutiny.
“But, Lord, you made me feel important,” she says, “And then you tried to erase us.” He love-bombed her, as any 19 year-old is susceptible to. But then he yanked it away, and tried to erase all evidence they were ever together.
2nd Pre-Chorus & Chorus: “You’re a Crisis of My Faith”
“Ooh, you’re a crisis of my faith,” she says, which ties together all the religious motifs in the song. Because of him, she lost her faith in men, in humanity, in herself, and in God.
He is the moment her “good girl faith” was thrown through the gauntlet, and it didn’t emerge unscathed.
“Would’ve, could’ve, should’ve,” she says regretfully, “If I’d only played it safe.” If she hadn’t taken a chance, she never would have been hurt so deeply. She could have avoided all this trauma if her faith hadn’t been shaken by him.
This pulls in one of Taylor’s central and most common metaphors: love as a game (see Blank Space, All You Had To Do Was Stay, et al). If she would have played a bit more cautiously, she never would have lost the match.
If she’d been more cautious in playing the love game, “I would’ve stayed on my knees.” Her faith wouldn’t have been broken, and she’d still retain her piety. She wouldn’t have lost faith in herself.
Bridge: “The Tomb Won’t Close”
The bridge describes a part of her that died because of him.
“God rest my soul,” she says, mourning her past self, “I miss who I used to be.” She lost a chunk of her identity with him that’s now long buried. She wants it back.
“The tomb won’t close” means that she can’t get over this loss. She keeps mulling it over, “digging up the grave” of her past self and examining it in the light.
“Stained glass windows in my mind” describes how she can’t see this past through rose-colored glasses. It’s a mosaic of pleasure and pain, and she can’t see it clearly through all the various colors.
This also alludes to a song that Taylor wrote and performed with Mayer, Half of My Heart. The music video takes place inside a church with stained glass windows, and Taylor uses this imagery as a metaphor for her inner turmoil and confusion.
“I regret you all the time,” she says. Even though there’s confusion over what happened and why it happened, it’s 100% colored with regret.
“I can’t let this go,” she says, “I fight with you in my sleep.” Even in dreams, she regrets him and tries to play out different scenarios.
🌌 Are you a Mastermind? Try my Midnights Lyrics Quiz! 🌌
“The wound won’t close,” she says, describing her continuing pain as an open wound. It’s still raw and still causes her trouble, like in this is me trying.
“I keep on waiting for a sign,” she says, scanning the heavens for a piece of karma or fate to tell her that she’ll be okay. This reflects her loss of faith that’s prominent on this album: she’s not praying to God, she’s looking for signs instead.
“I regret you all the time,” she repeats. The open wound still bleeds, and it bleeds regret.
Verse 3: “Give Me Back My Girlhood, It Was Mine First”
“If clarity’s in death, then why won’t this die?” she asks in the third verse. Part of her died as a result of their relationship, but the part of her that wants to go back and reverse the damage won’t die. It’s her trauma that she can’t get rid of.
Even after “years of tearing down our banners” – trying to forget, trying to shred every piece of her that was ever devoted to him – pieces of evidence still exist. And they exist in her trauma: these are her battle scars.
Now she’s “Living for the thrill of hitting you where it hurts.” She exists only for the thrill of punishing him like she was punished.
Dear John was one piece of this puzzle – a song that ruthlessly called him out on his predatory behavior. This song is likely another gut-punch aimed at him. It’s the only satisfaction she can get, after everything he did to her.
Like she says in Dear Reader, “when you aim for the devil, make sure you don’t miss.” And she hasn’t.
“Give me back my girlhood,” she screams, “it was mine first.” He stole her innocence, and she wants it back.
The tone of this line is like a toddler throwing a tantrum, which echoes her age at which her innocence was stolen. She was a kid, and never should have been preyed upon by an adult.
Swifties will point to virginity as the likely “girlhood” that he stole, but I think it’s more complex than that (and that’s also none of our business). He stole the part of her that thought love was good and pure. He stole her optimism. He stole her innocence, and now the rest of her life is colored by this pessimism.
Outro: “I Regret You All The Time”
The chorus repeats, then the bridge repeats in the outro twice.
This repetition is her rumination: she “can’t let this go.” It spins around and around in her mind. She looks for the pieces of her that died, asks for them back, and realizes she can’t have them, over and over.
She’s still an open wound, all these years later, which gives us a sense of just how damaging this relationship was.
She can never let go of the would’ve, could’ve, should’ves, and mulls over it like a broken record. It will never die, because she can never turn back time.
Would’ve, Could’ve, Should’ve Meaning: Final Thoughts
In the Midnight sleepless nights of Taylor’s life, Would’ve, Could’ve, Should’ve is a one of the most painful bouts of insomnia she’s ever had. It’s a heartbreak that will never resolve.
She spins through the stages of grief in this song: denial, anger, bargaining, and depression. She can just never reach acceptance. The “tomb won’t close” to allow that to happen.
It’s a gorgeous and heartbreaking rumination on grief: how it never goes away, how it changes your faith in love, and how pieces of you die each time you lose something important.
In Bigger Than The Whole Sky – which is lyrically and thematically linked to this track – she is finally able to reach acceptance with “I’m never gonna meet / What could’ve been, would’ve been / What should’ve been you.” She’ll never get to meet the person who she could have become had he not traumatized her.
But for now, in this track, she processes those first four stages of grief. She can’t move on to acceptance until she’s moved through denial, anger, bargaining, and depression, and that’s what she’s going through here, in the “stained glass windows in my mind.”
The only thing she’s sure about is regret, and that regret will never, ever die.
More Songs From Midnights
