It was 3:00 AM on October 21, 2022. Most of the world was processing the synth-pop gloss of Midnights, thinking they’d understood the assignment. Then, the 3am Edition dropped. Track 19 hit like a freight train. Within minutes, the Taylor Swift would’ve could’ve should’ve lyrics became a digital ghost story, haunting anyone who had ever looked back at a past version of themselves and felt a sudden, sharp pang of grief for the person they used to be. It wasn't just a "breakup song." Honestly, calling it a breakup song feels like a massive understatement, kinda like saying the Titanic had a little bit of a water problem.
The song is a visceral post-mortem of a relationship that happened when Swift was nineteen. It’s heavy. It’s loud. It’s drenched in religious imagery and the kind of regret that doesn’t just fade with a new album cycle.
The Age That Changed Everything
When you’re nineteen, you think you’re an adult. You aren't. Taylor has spent a lot of her career revisiting this specific era of her life, most notably in the ten-minute version of "All Too Well," but "Would’ve, Could’ve, Should’ve" feels different. It’s angrier. While many fans immediately linked the song to John Mayer—whom she dated briefly around that age—the song transcends the specific "who" and focuses on the "what." What happens to a girl when her girlhood is taken away before she’s done with it?
"I damn sure never would've danced with the devil / At nineteen," she sings. It’s a line that floors you. She isn't just blaming the guy; she's mourning the version of Taylor that didn't know better. We've all been there. You look back at a choice you made a decade ago and you just want to reach through time and shake yourself. But you can't. That’s the "ghost" she talks about in the bridge.
The production by Aaron Dessner is crucial here. It doesn't have the sparkly Jack Antonoff sheen of the rest of Midnights. Instead, it has this driving, frantic acoustic-rock energy that feels like a panic attack in slow motion. It builds and builds until she’s practically screaming about giving her "blood, sweat, and tears for this." It’s messy. It’s cathartic.
Religious Guilt and the Loss of "The Girl"
One of the most striking things about the Taylor Swift would’ve could’ve should’ve lyrics is the heavy use of religious metaphors. This isn't just about a bad date. She talks about "stained glass windows" in her mind. She mentions "the tomb." She calls the relationship a "crisis of my faith."
👉 See also: La Casa de los Famosos 2024 Voto: How Fans Actually Changed the Game This Season
For a girl who grew up in the public eye with a relatively "wholesome" image, the loss of innocence isn't just a personal milestone—it’s a public execution of an identity.
- The "God rest my soul" line isn't just a common phrase; it’s a plea.
- She compares the partner to a "devil" and herself to a "promising grownup" who got derailed.
- The imagery of "washing hands" suggests a desperate need to be clean of a memory that feels like a permanent stain.
If you’ve ever felt like a relationship didn't just break your heart but actually changed your fundamental chemistry, this song hits. It’s about the "would've" (the potential), the "could've" (the possibility), and the "should've" (the moral weight of the choice). It’s a trifecta of regret.
Why the Bridge is a Masterclass in Songwriting
The bridge. Oh, the bridge.
"Give me back my girlhood, it was mine first."
That single line sparked a million TikToks and essays. It’s the emotional core of the track. Swift often writes about the passage of time, but here, time hasn't healed anything. It has just calcified the resentment. She’s thirty-two writing about nineteen, and the wound is still bleeding. That’s the terrifying part of the song. It suggests that some things stay with you forever, no matter how many Grammys you win or how many stadiums you sell out.
She’s basically saying that she’s successful now, sure, but she’s still carrying the "shale" of that old relationship. It’s a weight. A ghost. A "weapon" she didn't know she was carrying.
Analyzing the Timeline and the "John Mayer" Factor
Look, we have to talk about the 19 of it all. Taylor Swift was nineteen when she dated John Mayer (who was thirty-two at the time). The math is hard to ignore, especially since the song is track 19 on the deluxe album. Swifties are basically FBI agents when it comes to these things. They noticed the parallels to "Dear John" immediately.
In "Dear John," she asked, "Don't you think nineteen's too young to be played by your dark, twisted games?"
In "Would've, Could've, Should've," she confirms, "I regret you all the time."
But focusing purely on the celebrity gossip misses the bigger picture. The song works because it’s universal. It’s for anyone who looked up to someone older, trusted them, and realized too late that the power dynamic was completely skewed. It’s a song about the "grownup" who should have known better, and the "child" who is left to pick up the pieces years later.
👉 See also: Historical Fiction Middle Ages: Why Most Authors Get the 14th Century Wrong
The Evolution of Swift's Songwriting Style
If you compare the Taylor Swift would’ve could’ve should’ve lyrics to her early work, you see a massive shift in how she handles trauma. Early Taylor might have written a "mean" song or a "sad" song. Midnights Taylor writes a "haunted" song.
There’s a sophisticated nuance here. She admits she was "determined" to run into the fire. She isn't claiming she was a passive victim with no agency; she’s acknowledging that her own youthful curiosity was the very thing that led her into the trap. That’s a much more complex, adult way of looking at a mistake. It’s not just "you did this to me," it’s "I can’t believe I let this happen to me, and I can’t forgive myself for it."
Misconceptions About the Song's Meaning
A lot of people think this song is about a current heartbreak. It’s not. It’s a "Midnights" song—part of a collection of songs about sleepless nights throughout her entire life. It’s a flashback.
Another misconception is that it’s a "hating men" anthem. It really isn't. It’s a "hating the loss of self" anthem. The anger is directed at the situation and the lasting impact of a mismatched power dynamic. It’s about the "God-forsaken mess" left behind when a "promising grownup" meets a "devil."
Practical Takeaways from the Song
While it’s a masterclass in lyricism, there are actually some pretty heavy life lessons tucked into those metaphors.
- Trust your gut, even when you're young. If it feels like you're "dancing with the devil," you probably are.
- Regret is a process, not a destination. It's okay to still be mad about something that happened a decade ago. You don't have to "get over it" on someone else's timeline.
- The "ghost" of your past self deserves grace. Taylor is hard on her nineteen-year-old self, but the song itself is a way of acknowledging that girl’s pain.
- Art is the ultimate exorcism. By writing this, she’s trying to "cast out" the ghost.
The song ends abruptly. There’s no resolution. No "and then I was fine." It just stops, leaving the listener in the same echoing room of memory where Taylor started. It’s uncomfortable because growth is uncomfortable.
📖 Related: Why the hood Mr Beast edit is taking over your feed
To truly understand the Taylor Swift would’ve could’ve should’ve lyrics, you have to listen to the song at high volume, preferably while driving alone or sitting in the dark. You have to feel the frantic pace of the drums. You have to hear the way her voice cracks when she says "mine first."
If you're looking to dive deeper into the lore, your next move should be a side-by-side comparison of this track with "Dear John" and "Manuscript" from The Tortured Poets Department. You'll see a clear, heartbreaking arc of a woman trying to reclaim her story from the men who tried to write it for her. Check the liner notes for the 3am Edition and pay attention to the production credits—Aaron Dessner’s influence is what gives this track its "folk-punk" heartbeat that sets it apart from the rest of her pop discography.