Tag Archives: Dylan O'Brien

Sad Girl Autumn: Taylor Swift’s Saddest Lyrics

The mornings are getting chilly. It’s time to start pulling the hats, scarves and plaid button-downs from the back of the closet. Pumpkin spiced lattes have returned — not caring if someone calls it basic. Combined with the re-release of Taylor Swift’s fourth studio album, Red (Taylor’s Version), it’s the season of “Sad Girl Autumn.”

Inspired by “Hot Girl Summer,” coined by rapper Megan Thee Stallion, “Sad Girl Autumn” embraces the sorrow, soul-searching and nostalgia of the fall season. Along with Swift, singer-songwriters Adele and Mitski also released music fitting the theme of “Sad Girl Autumn.”

To celebrate the season, I compiled a list of Swift’s 13 saddest lyrics to reminisce and weep about ahead of the release of Red (Taylor’s Version).

Track Fives

Every Swiftie knows track five is the most emotional, honest and vulnerable song on each album. It’s impossible to discuss Swift’s saddest lyrics without mentioning some of these tracks.

If I could insert the entirety of “All Too Well,” I would. It’s the ultimate track five and is often considered Swift’s best song. In five minutes, Swift revisits a gut-wrenching breakup that still stings years later. With its highly specific lyrics, including a scarf left behind, she reflects on the best and worst moments of a short-lived relationship. 

The original version of the song was 10 minutes long with explicit lyrics before it was trimmed down. However, the re-release of Red (Taylor’s Version) includes the uncut song, as well as a short film starring Swift, Sadie Sink and Dylan O’Brien.

Saddest lyric: And you call me up again just to break me like a promise / So casually cruel in the name of being honest

In “The Archer,” Swift explores her insecurities in a relationship and troubles trusting people. She admits to engaging in drama and acknowledges she never matured enough to deal with this. The song might also be a possible nod to her zodiac sign (Sagittarius) whose symbol is an archer.

Its lyrics are deep and personal with strong metaphors (being the archer and the prey), and an old children’s nursery rhyme (Humpty Dumpty) to call out enemies who were once friends.

Saddest lyric: Who could ever leave me, darling / But who could stay?

In an Instagram post, Swift explained “my tears ricochet” tells the story of an “embittered tormentor showing up at the funeral of his fallen object of obsession.” Fans have speculated the track alludes to selling her master recordings by Big Machine Records founder Scott Borchetta to record executive Scooter Braun.

The song’s funeral imagery could also represent Swift mourning the metaphorical death of her six albums now in the hands of Braun. Although she is artistically free at Republic Records, she sings in the bridge about losing her old musical home along with her original albums at Big Machine Records.

Saddest lyric: And I can go anywhere I want / Anywhere I want, just not home

In an interview with Apple Music, Swift revealed “tolerant it” was inspired by Daphne du Maurier’s 1938 novel Rebecca, in which a husband simply tolerates his wife while she goes out of her way for him. It’s a story about yearning for love and appreciation from someone who does not pay attention to you.

In the bridge, she confesses how much of a priority her husband is to her. He was someone she loved, worshipped and respected. However, her efforts remain unreciprocated and ignored.

Saddest lyric: I made you my temple, my mural, my sky / Now I’m begging for footnotes in the story of your life

Pure Heartbreak

While track fives are personal, emotional and usually the ones that make me cry like a baby, certain songs have more subtle sadness to their lyrics. Sometimes, they are songs that you didn’t realize you connected to until years later.

Part of the folklore teenage love triangle, “august” follows a summer romance doomed from the start. It’s told from the perspective of the girl James cheated on Betty with. The other songs related to this storyline include “cardigan” and “betty.”

It’s a song written for people who have an ex that wasn’t their ex because they never dated. For those who relate to this story, it creates a nice yet strange feeling. Every time I listen to this song, the bridge never fails to break me.

Saddest lyric: ‘Cause you weren’t mine to lose

Ever since listening to “happiness,” I have learned to trust songs with the word happy or happier (looking at you, Olivia Rodrigo). Reexamining a rotten relationship, the narrator also looks back on the better moments before everything went sour. However, it’s a hopeful song that views the bad times as once good times with good things to come in the future.

To me, it’s the perfect song for “Sad Girl Autumn.” It’s mournful yet promising despite all the pain and destruction of previous relationships. It’s about someone still searching for happiness (no pun intended), even though they know it’s a difficult journey.

Saddest lyric: When did all our lessons start to look like weapons pointed at my deepest hurt?

On a more optimistic note, “Begin Again” recalls past relationships while looking forward to new romances. It’s not always easy to move on, especially when insecurities and fears from previous partners always linger as well.

Even though it’s not the saddest song, the few aching moments are loud and clear. It’s the song with lyrics that feel like a stab in the heart if you understand exactly what Swift is saying.

Saddest lyric: He didn’t like it when I wore high heels, but I do

Similar to the previous song, “New Years Day” explores Swift focusing on the future and yearning for the memories. As the closing track on reputation, she appears ready to move on from the old drama and past mistakes.

In the bridge, she fears losing the person she’s falling in love with. These lyrics are reminiscent of “Enchanted” from her third studio album Speak Now, in which she hopes the person she wants isn’t in love with someone else.

Saddest lyric: Please don’t ever become a stranger whose laugh I could recognize anywhere

Folklore / Evermore

I will always love Swift’s sister records, folklore and evermore. The best way to describe my love for these albums is the same way I feel about “All Too Well.” If you don’t like these pieces of work, you probably don’t understand or appreciate the beauty of storytelling and poetry.

It doesn’t matter how many times I listen to “marjorie,” this track will always ignite a waterfall in my eyes. It’s deeply personal full of lessons learned years, as well as guilt for the times Swift didn’t have with her grandmother.

Saddest lyric: Should’ve kept every grocery store receipt / ‘Cause every scrap of you would be taken from me

Going back to the message of “my tears ricochet,” Swift’s regret concerning the loss of her masters and re-recording of her old albums continues in “coney island.” In a Twitter thread, one user interpreted the song as her apology to her old music.

While she attempts to reconnect with her past, the usage of Coney Island and its fading popularity work to represent her current situation and struggles. As mentioned earlier, Swift has artistic freedom at Republic Record, but she remains remorseful for how everything happened so quickly and so publicly.

Saddest lyric: But when I walked up to the podium, I think that I forgot to say your name

Have you ever listened to a song and felt like it was written specifically for you? That’s how I feel about “this is me trying.” It’s a song I hold near and dear to my heart because it’s so personal.

This track follows the narrator accepting wrongdoings while making an effort to improve, even if it goes unnoticed. Things aren’t perfect right now, the narrator knows that, so they are taking the first step to admit and fix things they should have done a long time ago.

Saddest lyric: They told me all of my cages were mental / So I got wasted like all my potential

An Ode to Mom

These last sets of lyrics are less sad lyrics to understand and more of a heartbreaking parallel between Swift and her mother. The mother-daughter duo always had a close relationship, which Swift first wrote about in “The Best Day.”

In the song, she revisits her childhood and teenage years. She recalls her mother taking her window shopping to escape bullying in middle school. She sings, “I don’t know who I’m going to talk to now at school / But I know I’m laughing on the car ride home with you.”

Over the years, Swift has also been open about her mother’s cancer diagnosis and health as a top priority. She later dedicated “Soon You’ll Get Better” to her mother and revealed it’s one of the hardest songs for her to write. In the bridge, she sings, “And I hate to make this all about me / But who am I supposed to talk to? / What am I supposed to do / If there’s no you?”

Of all her songs and lyrics, the parallel between these two songs is the most personal and meaningful. They are also universal because they are songs about wanting only the best for the person who has stayed by your side all your life.

Final Thoughts

As you celebrate the season of “Sad Girl Autumn,” remember Taylor Swift knows how to tug at the heartstrings by creating a collection of songs and lyrics that connect with so many people. It’s both powerful and terrifying. She also knows how to write a bridge you will scream into the void with tears streaming down your face.

Featured image by Bettina Mateo