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A deep dive into Taylor Swift’s most vulnerable songs
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Whenever Taylor Swift releases a new album, Swifties flock to see what track 5 will be called and make theories about what it’s about. This may sound strange if you’re not in the fandom, but Taylor Swift herself has said that the fifth track on each album is the most vulnerable song. In this article, we’ll take a deep dive into the significance of track 5s and what the fifth track on each album is about, with insights from Taylor Swift fandom creator Sofia Montañez.

What does track 5 mean to Taylor Swift?

According to Taylor Swift fandom creator Sofia Montañez, track 5 is the most emotionally vulnerable song on Taylor’s albums. This was initially a coincidence, but when fans pointed it out, Swift started doing this intentionally. With each album drop, fans are excited to hear track 5, as they’re often fan favorites.

Section 1 of 2:

The Significance of Track 5 on Taylor Swift’s Albums

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  1. Early on in Taylor Swift’s career, her fans noticed that her most devastating, emotional songs were always track 5 on their corresponding album. This was originally a coincidence, but once her fans pointed it out, Swift intentionally began placing her most vulnerable tracks in the 5th spot. Now, whenever she releases an album, fans eagerly wait to see what the song will be called and what it will be about because they know it will be raw and emotional.[1]
    • In an Instagram Live before the release of Lover, Swift said, “As I was making albums, I guess I was just kind of putting a very vulnerable, personal, honest, emotional song as track five.”[2]
    • As Montañez points out, “In Taylor’s own words, it’s the most vulnerable moment on the album. Just as 13 is her lucky number, 5 seems to represent the opposite for her.”[3]
    • “Track 5 isn’t always the most emotionally heavy or vulnerable song,” adds Montañez, “but it often carries deep emotional weight.”[4]
    • Most of Swift’s track 5s are ballads about heartbreak, but some are more upbeat and about falling in love.
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Section 2 of 2:

All of Taylor’s Track 5 Songs (So Far)

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  1. Cold As You” is the fifth track on Taylor Swift’s self-titled debut album. It follows Swift’s relationship with an emotionally closed-off ex-boyfriend. Throughout the song, she sings about how much she gave and how many times she tried to make the relationship work, but he continued to shut her out.
    • Emotionally devastating lyric: “You never did give a damn thing, honey / But I cried, cried for you / And I know you wouldn’t have told nobody if I died, died for you”
  2. 2
    White HorseWhite Horse” is track 5 on Swift’s sophomore album, Fearless. It follows Swift’s disappointment when her expectations for a relationship were not met. She once told Billboard, “It talks about falling in love and the fairy tales that you are going to have with this person, and then there is that moment where you realize that it is not going to happen. That moment is the most earth-shattering moment.”[5]
    • Emotionally devastating lyric: “My mistake, I didn’t know to be in love / You had to fight to have the upper hand”
  3. 3
    Dear John Speak Now’s “Dear John” was Swift’s most mature track 5 to date at the time of its release. While Swift has not confessed who the song is about, most assume it’s about her relationship with fellow singer John Mayer.[6] The song tells the story of a manipulative relationship in which the girl is much younger and more naive than her partner. Swift sings about ignoring her mother’s warnings and her partner’s mind games in hope that the relationship would work.
    • Emotionally devastating lyric: “You are an expert at sorry and keeping lines blurry / Never impressed by me acing your tests / All the girls that you’ve run dry have tired, lifeless eyes / ‘Cause you burned them out”
  4. 4
    All Too Well Perhaps her most iconic track 5, “All Too Well” is an emotional song on the album Red. It is likely about Swift’s relationship with Jake Gyllenhaal and tells the story of a failed relationship that Swift can’t forget or get over.[7] She remembers small details and intimate moments clearly and wonders if the relationship impacted her ex as much as it did her.
    • Emotionally devastating lyric: “Time won’t fly, it’s like I’m paralyzed by it / I’d like to be my old self again / But I’m still trying to find it”
    • This song was an immediate hit with fans, though it was never released as a single. Fans loved it so much, in fact, that Swift released a 10-minute version on Red (Taylor’s Version).
  5. 5
    All You Had to Do Was Stay 1989’s “All You Had to Do Was Stay” was a departure from Swift’s previous track 5s, as it was an upbeat pop song. Despite its sound, though, it’s not a happy love song. In the song, Swift sings about the heartbreak she felt when her ex left. While he later tried to get back with her, it was too late, and the damage was already done.
    • Emotionally devastating lyric: “Hey, all you had to do was stay / Had me in the palm of your hand, then / Why’d you have to go and lock me out when I let you in?”
  6. 6
    DelicateDelicate” was Swift’s first track 5 that was about falling in love rather than a breakup. On the surface, Reputation was an album about revenge, but many of the songs were actually about Swift secretly falling in love with Joe Alwyn while hiding away from the public. At the album’s release party, Swift said, “It’s like what happens when you meet someone who you really want in your life, and then you start worrying about what they’ve heard before they met you? You start to wonder like, ‘Could something fake, like your reputation, affect something real like someone getting to know you?”[8]
    • Emotionally devastating lyric: “This ain’t for the best / My reputation’s never been worse, so / You must like me for me”
  7. 7
    The Archer Lover’s fifth track, “The Archer,” was Swift’s first track 5 that wasn’t directly about a romantic relationship. The song is about Swift’s insecurities and her fears that she might accidentally sabotage her relationship. She’s always waiting for the other shoe to drop, even though she knows her behaviors will likely lead to the end of the relationship.
    • Emotionally devastating lyric: “I wake in the night, I pace like a ghost / The room is on fire, invisible smoke / And all of my heroes die all alone / Help me hold onto you”
  8. 8
    My Tears Ricochet Folklore’s “My Tears Ricochet” is about the betrayal of a man Swift viewed as family, likely Scott Borchetta, the founder of her first record label, who refused to sell her music back to her.[9] In the song, Swift compares her situation to an abusive husband showing up at his wife’s funeral, pretending to be sad while knowing how much pain he caused her.
    • Emotionally devastating lyric: “I didn’t have it in myself to go with grace / And so the battleships will sink beneath the waves / You had to kill me, but it killed you just the same / Cursing my name, wishing I stayed / You turned into your worst fears”
  9. 9
    Tolerate It The fifth track on Evermore, “Tolerate It,” was inspired by Daphne Du Maurier’s book Rebecca. Both the song and the book follow a woman whose husband doesn’t appreciate her, no matter how hard she tries to prove her love to him. Swift said, “When I was reading Rebecca by Daphne Du Maurier, I was thinking, ‘Wow, her husband just tolerates her. She’s doing all these things and she’s trying so hard and she’s trying to impress him, but he’s just tolerating her… There was a part of me that was relating to that.”[10]
    • Emotionally devastating lyric: “If it’s all in my head, tell me now / Tell me I’ve got it wrong somehow / I know my love should be celebrated / But you tolerate it”
  10. 10
    You’re On Your Own, KidYou’re On Your Own, Kid” from Swift’s 10th album Midnights may have sparked the friendship bracelet trend at the Eras Tour, but it’s also much deeper than that. It’s a bittersweet song in which Swift looks back on different points in her life, good and bad. She feels alone but eventually realizes that being self-reliant is empowering.
    • Emotionally devastating lyric: “From sprinkler splashes to fireplace ashes / I gave my blood, sweat, and tears for this / I hosted parties and starved my body / Like I’d be saved by a perfect kiss”
  11. 11
    So Long, London While most of The Tortured Poets Department is supposedly about Swift’s short-lived fling with The 1975 singer Matty Healy, “So Long, London” is likely about her breakup with long-time boyfriend Joe Alwyn.[11] In the song, Swift sings about leaving London, England, where she was living most of the time during their relationship. Her partner wasn’t putting as much effort into the relationship as she was, and though she has moved on, she still feels angry over how much time she thinks she wasted in the relationship.
    • Emotionally devastating lyric: “And you say I abandoned the ship / But I was going down with it / My white knuckle dying grip / Holding tight to your quiet resentment”
    • What to know which TTPD song you are? Take our quiz to find out!
  12. 12
    Eldest Daughter Swift’s newest album, The Life of a Showgirl, features the song “Eldest Daughter” in the coveted track 5 slot. She described each song on Amazon Music and had this to say about “Eldest Daughter:” “It’s a love song about kind of the roles that we play in our public life because, nowadays, everyone has a public life… And it’s really hard to be sincere publicly because that’s not really what our culture rewards…This song really kind of gets to the heart of when someone gets close enough to you to earn your trust. That’s when you can admit to them that you actually really do care about some things.”[12]
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About This Article

Sofia Montañez
Co-authored by:
Taylor Swift Fandom Content Creator
This article was co-authored by Sofia Montañez and by wikiHow staff writer, Raven Minyard, BA. Sofia Montañez is a Taylor Swift fandom content creator based in Monterrey, Mexico. With over 5 years of experience creating content, Sofia is known as Swift Better Have My Money on social media. Her content has a fashion focus, sharing fashion videos that offer a dupe for a Taylor Swift outfit or recreates a Taylor Swift album cover or photoshoot. With nearly 75k followers on Instagram, Sofia is also a LaceMade ambassador. She has a bachelor’s degree in Communications from Universidad Autónoma de Nuevo León and currently works as a marketing executive for Apetit Catering.
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Co-authors: 2
Updated: October 23, 2025
Views: 222
Categories: Music Appreciation
Thanks to all authors for creating a page that has been read 222 times.

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