Home » Albums » Midnights » Songs on Midnights » Would’ve, Could’ve, Should’ve

Would've, Could've, Should've

Bonus Track | Midnights (3am Edition) [2022]

“Would’ve, Could’ve, Should’ve” is the nineteenth track on Taylor’s tenth studio album, Midnights (2022). It is also the sixth bonus track on the 3am Edition of the album. Written and produced by Taylor and Aaron Dessner, the song has her reeling back to past mistakes when she was nineteen.

Background and Release

On August 28, 2022, Taylor announced her tenth studio album, Midnights, set for release on October 21, 2022. On October 16, she posted a short video on her social media that presented a schedule of the days leading up to the album release, entitled “Midnight Manifest”. On it, Taylor also teased a “special very chaotic surprise” happening three hours after the albums release. This materialized into a digital and streaming only version of the album, titled Midnights (3am Edition), containing an additional seven songs that according to Taylor were written but removed to keep the album at 13 songs. One of those songs is “Would’ve, Could’ve, Should’ve.” Taylor said:

«I think of Midnights as a complete concept album, with those 13 songs forming a full picture of the intensities of that mystifying, mad hour. However! There were other songs we wrote on our journey to find that magic 13. I’m calling them 3am tracks. Lately I’ve been loving the feeling of sharing more of our creative process with you, like we do with 'From The Vault' tracks. So it’s 3am and I’m giving them to you now.»

Taylor Swift

Lyrical Theme

According to co-writer and co-producer Aaron Dessner, “Would’ve, Could’ve, Should’ve” was written in March 2021, when he was staying at Taylor’s home in Los Angeles ahead of the Grammy Awards (where they would win the “Album of the Year” award for folklore). Aaron told the podcast Broken Record in April 2023:

«I think the best song we've ever written is called 'Would've, Could've, Should've'. We wrote that song together, and recorded it, while we were together in LA for the folklore Grammys. So it goes back that far. And the same goes for 'High Infidelity'. Those songs we actually recorded in her house then. And eventually she obviously made most of Midnights with Jack and it became something different, but we made 'Would've, Could've, Should've, 'High Infidelity', 'The Great War' and 'Hits Different' together. And it was great to be a part of that record in that way. It was really special.»

Aaron Dessner

The title “Would’ve, Could’ve, Should’ve” is a classic phrase to emphasize all the things that could have gone differently in a certain situation. In this case, the song is widely expected to be about the relationship between Taylor and John Mayer in 2009. She was nineteen at the time, John Mayer was 32.

“Would’ve, Could’ve, Should’ve” is a powerful sequel to 2010’s “Dear John,” a song in which she first revealed the alarming power imbalance between the two. This song is messier, more confused, and more ambivalent, as Taylor struggles to understand the brash, complex 19-year-old she used to be. Whilst the age gap in the relationship was heavily criticized at the time, Taylor ignored all warning signs. She was starstruck and just bursting on to the music scene, which he took advantage of. Now, looking back on this relationship as a 32-year old woman herself, she feels deep regret and as if part of her was stolen.

Live Performances

“Would’ve, Could’ve, Should’ve” received its first live performance acoustically on guitar on May 7, 2023, in Nashville during one of Taylor’s shows on “The Eras Tour” (2023-2024). Aaron Dessner was the surprise guest and accompanied her on a second guitar. It was the third time he joined Taylor on stage during the tour. Afterwards, he shared on Instagram:

«Last night in Nashville I got to play my favorite song Taylor and I have written together, 'Would've, Could've, Should've', at 1:30am in the middle of a giant rainstorm – while also getting to see the whole show (Phoebe Bridgers came out to play 'Nothing New' with Taylor which we all made together!) – which only ended at 2am due to rain delays. Not sure how I got so lucky to have these experiences on the greatest tour of all time, but I'm so thankful. It's incredibly inspiring to see the dedication and work ethic Taylor, her band, her dancers and her incredible team and crew put into this show. It's truly a mind blowing experience.»

Aaron Dessner

When Taylor covered People‘s 2023 “Most Intriguing People of the Year” issue, Aaron opened up about his collaborations and friendship with her. When asked what it was like for him to join Taylor as a surprise guest on tour, he said: “It’s really hard to describe what it feels like to be raised up on a hydraulic into a stadium of 80,000 fans who have already been experiencing the best concert they have ever seen for two and a half hours, as I would join Taylor onstage towards the end of the show. But Taylor was so generous in her introductions and it’s really such a special moment for us to be able to play some of these songs acoustically for her fans. It’s hard to describe how exhilarating it was to play ‘Would’ve, Could’ve, Should’ve’ in the pouring rain acoustically in Nashville.”

Taylor performed the song again on February 26, 2024, during her final Australian show on “The Eras Tour” in Sydney. She performed it as an acoustic guitar mashup with “ivy” (2020). On June 7, 2024, she sang it together with “I Know Places” (2014) in Edinburgh.

Commercial Performance

In the United States, songs from Midnights occupied the entire Top 10 of the Billboard Hot 100; a historic feat. “Would’ve, Could’ve, Should’ve” debuted at No. 20 on the chart. Taylor became the first artist to simultaneously occupy the Top 10 spots of the Hot 100; the female artist with the most Top 10 songs (40); and the first act to occupy the entire Top 10 of the Hot 100, Streaming Songs, and Digital Songs charts simultaneously. Midnights also became the first album in history to contain ten Top 10 songs.

Lyrics

[Verse 1]
If you would’ve blinked then I would’ve
Looked away at the first glance
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?

[Pre-Chorus 1]
Oh, all I used to do was pray
Would’ve, could’ve, should’ve
If you never looked my way

[Chorus]
I would’ve stayed on my knees
And I damn sure would’ve never danced with the devil
At nineteen, 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’d left me wondering

[Verse 2]
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

[Pre-Chorus 2]
Oh, you’re a crisis of my faith
Would’ve, could’ve, should’ve
If I’d only played it safe

[Bridge]
God rest my soul
I miss who I used to be
The tomb won’t close
Stained glass windows in my mind
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

[Verse 3]
If clarity’s in death, then why won’t this die?
Years of tearing down our banners, you and I
Living for the thrill of hitting you where it hurts
Give me me back my girlhood, it was mine first

[Final Chorus]
And I damn sure would’ve never danced with the devil
At nineteen, 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’d left me wondering

[Outro]
Oh, god rest my soul
I miss who I used to be
The tomb won’t close
Stained glass windows in my mind
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