top of page

The Love Eras of Taylor Swift

Updated: Feb 14, 2023

By Camilla De La Cruz

Often credited as one of the best songwriters and lyricists of the generation, Taylor Swift has crafted a career most could only dream of. With recording breaking charts history and ticket sales for her upcoming Era’s tour, it’s easy to ask how she gained this much popularity. The answer: a long, impressive discography and a dedicated fan base who are willing to look between the lines to interrupt Taylor’s storytelling in her music.

A new country star

Inspired by country acts such as Faith Hill, Dolly Parton and more, Taylor moved to Nashville, commonly known as the “city of country music” to start her career at the young age of 14. At 16, she released her debut album self-titled.

As a young girl in a genre male-dominated genre, Taylor attracted a younger female audience to her music and to country music in general. Her debut and sophomore albums included key characteristics of country music, including the iconic banjo and fiddles, familiar structure and of course storytelling, which has stuck with Taylor even after her departure from the genre and introduced many new people to country music.

Her first two albums would garner moderate success, but as she began releasing hits such as, “Love Story” of her sophomore album, Taylor began merging her way into the mainstream.

Oh, my, love is a lie

By 2008, Taylor had created a reputable name for herself in the music industry. So, news about her dating Disney star Joe Jonas made big headlines in the entertainment industry. The relationship didn’t last long as Joe called it quits after a short 27-second phone call. Taylor records her emotions about the breakup in her song “Last Kiss” where she cleverly includes a 27-second intro alluding to the length of her phone call. She also mentioned, “the guy who broke up with me on the phone” in her iconic SNL monologue song and in an interview with Ellen DeGeneres.

Taylor Swift on Saturday Night Live in 2009 -

It's important to note that Taylor was only 18 when the relationship went public. At such a young age, it must’ve been difficult to figure out the balance between how much she shares in her songs about her relationships and how much she keeps private. This balance changes throughout her career and it's interesting to see how it shifts through her albums.

Singer to Actor

Taylor began spreading her horizons in 2009, making her acting debut on the romantic comedy Valentine's Day, where she worked with Taylor Lautner, most famously known for his work in the Twilight franchise. The pair became lovers on and off screen and once again the couple became a hot topic in pop culture. Not to mention the fact the two stars shared the same name, thus catching the ship name “Taylor squared”. Unfortunately, this one wasn’t meant to be yet again, but this ended on a more forgiving note rather than a negative one.

Swift acknowledges this relationship in her song “Back to December” where she for the first time apologises to her ex and admits her wrongdoing, showing how she matured as a songwriter.

“I've never apologized to someone in a song before. In the good, or bad, or the apology, the person I wrote the song for deserves this.” - Taylor Swift

I remember it All Too Well

“All too well” came back to the limelight after the re-release of Taylor’s fourth studio album Red in 2021, with a full 10-minute version and a short film starring Sadie Sink and Dylan O’Brien. The song is supposedly about her short relationship with actor Jake Gyllenhaal, along with some other songs in the Red album.

There were numerous reasons that made their relationship tense. Allegedly, Jake didn’t show up to Taylor’s 21st birthday party which obviously upset Taylor. This inspired the line “and it’s supposed to be fun turning twenty-one”. The incident could’ve also inspired the song “22” as her twenty-second birthday would’ve replaced the disappointment of her previous birthday.

Taylor's songs are also well known for including extensive detail as part of her storytelling. In 10 minutes, she’s able to incorporate extensive details, such as leaving her red scarf at Jake’s sister’s house (Taylor mentions might still be with Jake to this day), and things as basic as the weather in her songs. Like any novel or poem, this amount of detail allows her audience to step into her shoes.

It’s also important to note that there was a large age gap between Taylor and Jake. While Jake was 29-30, Taylor was only 20-21. She makes a reference to this in the line, “the punchline goes ‘I’ll get older, but your lovers stay my age’”, alluding to the age of Jake's current girlfriend Jeanne Cadieu who is 25. Taylor depicts this tension of the age gap in her short film in scenes where she was left out of conversations with Jake's older friends and her not being able to drink with those friends, and then in arguing scenes throughout the film. As well, there was a similar age gap between the actors as Dylan was 30 years old while Sadie was only 19 in 2021. This was likely intentional by Taylor to make her audience a bit uncomfortable when viewing this age gap.

Image from “All too well” short film -

Are we out of the Woods?

Taylor’s next album titled 1989 named after the year she was born would signify Swift’s separation from country as she released her first full pop album in 2014.

Although never confirmed, the album is widely speculated to be about Taylor's relationship with former One Direction member Harry Styles. With paparazzi shots of the pair in NYC Central Park spread, the internet couldn’t contain its excitement. Even if many on the internet were convinced that they were a “match made in heaven”, due to the large popularity surrounding the duo, the relationship would quickly fall apart in early 2013 after an argument during a holiday on a private island.

Many fans believe that “Out of the Woods”, and the appropriately titled “Style” were about this relationship. Taylor Swift herself tells the Grammy Museum that she felt anxious during the majority of her relationship with Harry, which explains the repetition of the lyrics, “are we out of the woods… are in the clear yet” during the chorus. But what sets Taylor Swift apart from other artists is her ability to craft beautiful bridges, and “Out of the woods” is no exception. Taylor is known for her incredible storytelling in her songs, so the bridge acts as the climax of the story and the most captivating part of the story and the song.

But she may have not been done talking about this relationship with 1989. In her latest album Midnights, Taylor places a self-sample of “Out of the Woods” in “Question…?”, leading some fans to speculate that this new song may be about her feelings throughout the relationship even after almost 10 years since pictures at Central Park. As well, the lyric “last December” in Out of the Woods has to be a reference to the song of the same name. One thing is for sure, Taylor definitely knows how to keep her audience on the edge of their seats.

My reputation has never been worse

Throughout her career, Taylor has been criticized for focusing too much on her romantic relationship in her songwriting and for dating many famous high-profile celebrities. This garnered a negative reputation (pun intended) for her image. She addresses these comments by stating that romantic relationships are a very common topic in songs, but critics rarely make comments when this happens to male singers.

“Frankly that’s a very sexist angle to take. No one says that about Ed Sheeran. No one says that about Bruno Mars. They’re all writing songs about their exes, their current girlfriends, their love life, and no one raises the red flag there”

Comments like these reveal a sad reality faced by women, especially in the entertainment industry. Women in particular are more susceptible to negative backlash for engaging in frequent romantic relationships and having sexist labels put on them and Taylor was no exception.

Cover of magazine Famous (2012), reporting false rumours that she was pregnant

After public feuds with various celebrities in 2016, Taylor's image fell from a pure country star to a greedy celebrity. Her public persona was now being portrayed as a “serial dater”, over-dramatic and sometimes even crazy. Her image and storytelling were now out of hand.

“No one physically saw me for a year. And I thought that’s what they wanted” – Taylor in her Miss Americana documentary.

Taylor addressed her ruined persona in the latter half of the music video for “Blank Space”, where she throws valuable tableware and even breaks a car, as well as making multiple references to her “long list of ex-lovers” (no, not her Starbucks lovers, sorry).

And there’s no doubt that this had a deep impact on Taylor in the long run. In one of her most vulnerable songs yet “Anti-hero”, Taylor described how she feels like a burden and not good enough. She describes overthinking at night and depression “When my depression works the graveyard shift, all of the people I’ve ghosted stand there in the room. The lyric “I’ll stare directly at the sun but never in the mirror” described her self-hatred as she can’t bear to tolerate herself and her weaknesses, obviously a very hard thing to go through. But it's songs like “Anti-hero” that prove that yes, Taylor can write songs outside of romantic relationships.

A different kind of love

After Lover, Taylor began to shift from writing from her own experiences and began to write fictional stories. Most noticeable in her album Folklore which includes songs that she dubs as “The Teenage love Triangle” consisting of “Betty”, “August” and “Cardigan”. These songs are written from the perspective of 17-year-old James and his drifting summer romance with popular girl Betty. Fictional storylines within mainstream music have lost their popularity over the years, so seeing Taylor incorporate fiction in her music was something refreshing for her fans to enjoy. Perhaps she learnt to not call out or to not write songs that are too personal in order to keep some privacy when under media scrutiny. Disappointing for some, because vulnerability in one’s art can make it more authentic and real to the artist.

“I’m the only one who knows what these songs are really about. It’s the one shred of privacy I have in the matter” – Taylor speaking with Time magazine

A rare phenomenon

Taylor had a one-of-a-kind musical career. To be able to withstand so many years despite multiple adversities is a challenge. To use this as inspiration for her art, to relieve the pain of past relationships and feelings caused at every performance is another. To mark her emotions of heartbreak, love, and fear in such a compelling way by including extensive detail in her lyrics. Although yes, many other artists write about similar topics as Taylor and write just as compelling storylines in their songs, not many are able to replicate Taylor’s ability to keep fans invested in her storytelling.

With the success of her latest album Midnights, the Billboard crowned artist of the 2010s is back.


Recent Posts

See All


bottom of page