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16 Saddest Taylor Swift Songs That Will Break Your Heart

Taylor Swift’s music’s brilliant lyricism and narrative-driven nature have made her a well-known singer and songwriter in the United States. Throughout the course of her professional life, she has experimented with a variety of genres.

There’s no denying that she’s one of the most excellent musicians of her generation, even though she might be regarded as Hollywood’s “undateable” sweetheart.

In this article, I’d like to take you through some of my favorite songs she is known for writing that are exquisitely depressing. Prepare your tissues as I count down the top saddest songs of Taylor Swift of all time.

1. Ronan

“Ronan,” recently released in “Taylor’s Version” by Taylor, opens the show. Before Taylor’s straightforward chords. The lyrics she sings are melancholy and haunting. The musician is a master of melody, creating simple pieces for her songs that are incredibly catchy and satisfying to listen to. Beautiful interplay will make you cry.

2. Last Kiss

If you thought that “Ronan” was the most depressing thing that had ever happened, you are gravely mistaken. One of the best – or perhaps worst – songs to listen to if you’re going through a challenging breakup is “Last Kiss,” which is a tragic farewell to the lover who got away.

3. I Almost Do

You are encouraged to indulge in your feelings of melancholy for a short while by the song “I Almost Do,” which has a folky and almost country sound. There is a nice contrast between the sad lyrics and the nearly upbeat backing track characteristic of the sound associated with Taylor Swift.

The song “I Almost Do” is about overcoming the temptation to get back together with an ex-lover despite the knowledge that you and your exes will never be a healthy match for one another.

Like much of what Taylor sings about, this is something to which many of us can relate because she writes about the human experience. The human experience is a common theme in Taylor’s music.

4. All Too Well

The song “All Too Well,” with its delicate electric guitar arpeggios and gentle, persistent acoustic guitar strumming, will captivate you and submerge you in its melancholy from the moment the first note is played. It is one of the rawest breakup songs you’ll ever hear.

The verses sung in Taylor’s signature delicate tone are broken up by interspersed guitar solos that give this track an atmosphere reminiscent of country music. The song is full of heartbreak.

It is not difficult to understand why All Too Well is considered one of Taylor’s most popular songs. This song will stay in your head for days, whether for the better or the worse, because the chorus is so irresistibly catchy and the chord progression is so straightforward.

5. Come Back, Be Here

“Come Back… Be Here” by Taylor talks about wanting a lover we can’t have, which is a feeling we’ve all had.

Her country roots are evident in this song, which has a simple melody and classic chord progression. As you probably know, Taylor began as a country singer. It’s an iconic example of the country saying, “give me three chords and the truth.”

6. The Moment I Knew

“The Moment I Knew” is a piano ballad with a beautiful cello accompaniment. It’s similar to Taylor’s other works but also very different.

Taylor Swift’s verses are accompanied by a cello pseudo-countermelody. This emphasizes her lyrics. Epic instrumentation and Taylor’s powerful vocals pull at the listener’s heartstrings in the chorus.

7. Dear John

Undoubtedly, “Dear John” has a country vibe, harkening back to Taylor’s roots as a country singer. This song features prominent acoustic guitar work and is complemented by electric guitar riffs that add a touch of sonic soul.

8. Sad Beautiful, Tragic

Taylor Swift’s music is straightforward and easy to understand. The singer provides a contrast between sad lyrics and upbeat music with his or her performance. Consider the song “Sad Beautiful Tragic,” in which an acoustic guitar plays a chord progression and a second guitar plays a simple, lilting melody. It has no chorus. Instead of a break between verses, there is a brief musical interlude.

9. Breathe

Colbie Caillat’s incredible vocal abilities are showcased on “Breath,” and her duet with Sia creates a haunting, melancholy song that almost makes you want to get up and dance.Another song that harkens back to Taylor’s time as a country singer, with its straightforward melody, effortless harmonies, and straightforward chord progression.

10. Never Grow Up

I wanted to end this list with a song from Taylor’s early days. “Never Grow Up” is a love song, but to a child. It describes the desire all parents have to keep their children young and innocent. It’s about the little things kids do that make us happy. “Never Grow Up” will move parents.

11. White Horse

Who cried to this song about a nonexistent ex? I first remember Taylor’s music video sobs. This song shows Taylor’s imperfect relationship. Not princes. “White Horse” self-blames for a failed relationship. “Stupid girl, I should’ve known,” and “My mistake, I didn’t know to love/fight” Taylor’s attitude shifts. Ex-lover grovels on the bridge.

Taylor is unapologetic. (I’ll find someone) She’s riding solo to be happy. Taylor is moving on without “White Horse” Fast!

12. Back to December

“Back to December” is a song by American singer-songwriter Taylor Swift, from her third studio album, “Speak Now” released in 2010. The song is recognized as an apology—an act of contrition—making it the first time Swift ever apologized in a song. Lyrically, “Back to December” addresses a past lover she treated poorly and now regrets letting go.

Although Swift never officially confirmed the person’s identity, the song is widely believed to be about her ex-boyfriend Taylor Lautner, due to numerous clues in the lyrics that align with their known relationship timeline. The song received widespread acclaim from music critics who highlighted its vulnerable and honest lyrics. Its accompanying music video depicts Swift’s melancholy and regret as she longs to go “Back to December” and correct her past mistakes. The song showcases Swift’s maturation as a songwriter and willingness to explore more complex emotional territory in her music.

13. Teardrops On My Guitar

“Teardrops on My Guitar” is a song by American singer-songwriter Taylor Swift, from her eponymous debut album released in 2006. The song is based on Swift’s real-life experience with a boy named Drew during high school, whom she had feelings for but who was oblivious to her affection.

The song is one of the earliest examples of Swift’s narrative storytelling abilities, combining personal experiences with a catchy country-pop melody. “Teardrops on My Guitar” was highly successful, becoming Swift’s first major hit and helping to establish her as a breakout star in country music. It peaked at number 13 on the Billboard Hot 100 and number two on the Hot Country Songs chart. The song has been praised for its emotional depth and relatability, effectively communicating the universal feelings of unrequited love and heartache. It has since become one of Swift’s most recognizable and enduring hits.

14. Exile

“Exile” is a song by American singer-songwriter Taylor Swift, featuring Bon Iver, from her eighth studio album, “Folklore,” released in 2020. The song is a melancholic duet that explores the end of a relationship through both parties’ perspectives, effectively capturing feelings of heartbreak, regret, and misunderstanding.

Swift and Bon Iver, the stage name of Justin Vernon, exchange verses, creating a conversational narrative filled with potent imagery and emotion. The instrumentation is primarily piano-driven, providing a haunting and somber backdrop to the lyrics.

“Exile” was widely praised by critics for its emotive vocal performances, lyrical depth, and melancholic ambiance. The song was seen as a significant shift in Swift’s musical direction, demonstrating her ability to branch out into more indie and folk-influenced sounds while maintaining her knack for storytelling.

15. Forever & Always

“Forever & Always” is a song by American singer-songwriter Taylor Swift from her second studio album, “Fearless”, released in 2008. The song was written in response to a sudden end of a relationship, widely speculated to be with pop singer Joe Jonas.

Swift’s lyrics vividly describe the confusion and heartbreak felt when someone abruptly leaves without providing a proper closure.

Musically, it’s a pop-rock number with country influences, showcasing the dramatic flair and emotional storytelling that Swift has become known for. The song received generally positive reviews from music critics who praised its candid lyrics and Swift’s emotive delivery.

Additionally, “Forever & Always” was re-recorded in a stripped-down, piano version for Swift’s “Fearless (Taylor’s Version)” in 2021, offering a more mature and reflective perspective on the intense emotions felt during the original recording.

16. Soon You’ll Get Better

“Soon You’ll Get Better” is a deeply emotional song by American singer-songwriter Taylor Swift, featured on her seventh studio album, “Lover”, released in 2019. The song features the Dixie Chicks (now known as The Chicks), marking one of their significant collaborations before their own comeback.

The lyrics are a poignant reflection on Swift’s experiences with her mother’s battle with cancer, making it one of her most personal and heartbreaking songs to date. “Soon You’ll Get Better” is an acoustic ballad that expresses Swift’s hope, fear, and desperation about her mother’s health condition.

Critics praised the song for its raw honesty and emotional depth, and many fans found it relatable in the context of their own experiences with illness in their families. Swift has expressed that the song was difficult to write and perform, underlining its deeply personal significance.


Voilà. This has been fun, and hopefully, Taylor Swift’s saddest songs are behind her. She’s nearing marriage and, hopefully, long-term happiness. It would be nice if she stopped making lemonade from her failed relationships. She’s running on ever-older memories, so she should let go. Taylor, write happy things, and we’ll still love you.

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