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Taylor Swift's evolution from Heartbreak Princess and a long list of ex lovers

Taylor Swift is on top of the world and it is impossible to keep up with her even if you are spinning in your highest heels. It has been 19 years since she signed her first record deal. After signing her name on the dotted line, there’s been no stopping her. Whether you know Taylor Swift’s lyrics off by heart, or stumbled upon the singer by chance – she’ll have an everlasting effect on you.

So who is Taylor Swift? Well, she’s the cultural phenomenon of the 21st century whose plethora of breakup anthems speaks volumes to generations. The ‘anti-hero’ who has remade herself despite media trials and broke all records to prove she encompasses the ‘music industry’. She’s also the artist who manages to dig three layers deep into her vulnerability and accept her illicit affairs with every new album. Or perhaps she’s simply the 33-year-old celebrity who can perform 44 songs night after night for sold-out stadiums, and enchant millions of fans leaving them with no Blank Space but a lifetime of treasure-trove memories. It’s hard to describe Taylor in one word, let alone a feature, but we’ll try.

The beginning of Taylor Swift

Taylor Swift mania can probably be boiled down to four things, lyrics, ex-boyfriends, her movie and re-recording her albums.

Taylor’s big break came at the age of 14 when she signed with Big Machine Records. She went on to release six albums under the label including her self-titled debut album, Taylor Swift ,which debuted at number five on the US Billboard 200.

The album went on to make history as it stayed in the Billboard 200 for 157 weeks, making it the longest by any release in the US during the 2000s.

The Our Song crooner also became the first female country music artist to write or co-write every track on a US platinum-certified debut album.

She is Fearless

Taylor Swift’s Fearless took the music charts by storm. It was her first number-one album on the Billboard 200 and quickly cemented itself as 2009’s top-selling album in the US.

The track You Belong with Me was the album’s highest-charting single on the Hot 100 as well. It peaked at number two and became the first country song to top Billboard’s all-genre Radio Songs chart.

And I don’t know how it gets better than this.

But it did.

Speak Now to Reputation, the formation era

After Fearless, Taylor Swift’s lyrics finally became noticed outside her loyal following. Finally, people were listening.

Her next venture, Speak Now, sold one million copies and graced the Top 200. The 20-something-old country singer’s mature approach in the album made critics pour praise.

Rob Sheffield of Rolling Stone wrote: “In a mere four years, the 20-year-old Nashville firecracker has put her name on three dozen or so of the smartest songs released by anyone in pop, rock or country.”

Fearless and Speak Now were only the beginning, as the widespread craze only continued to grow with her next albums like Red, with 1.21 million sales.

Big Reputation

Looking back, Taylor Swift’s Reputation was THE moment that foretold, just like in her lyrics, why so many fade but she will stay. The singer took a hiatus from social media for a year and came back with Reputation in 2017. While haters predicted the Swift era ended and the upcoming album wouldn’t leave a mark on the charts.

But the Bad Blood hitmaker proved her influence wasn’t going anywhere. It debuted atop the Top 200 with 1.21 million sales, making Tay Tay the first act to have four albums sell one million copies in a week.

Lover to Midnights

Taylor’s new era of owning her own music came with her seventh studio album Lover. After she left Big Machine Records she signed with Universal Music Group. Her subsequent albums and re-records of old albums including, Red Taylor’s Version (TV), Fearless (TV) and Speak Now (TV), have maintained their good ol’ number one spot. They were the only re-records in history to ever achieve this feat.

Taylor Swift dropped Midnights in 2022 and proved that she can still make the whole place shimmer. It appears striving to make history is now a yearly ritual for Tay Tay. Her tenth studio album Midnights was dubbed as an ‘instant classic’ and went on to break all records. 10 songs from the record monopolized the entire top 10 of the Billboard Hot 100 chart at the time. Needless to say, she became the first artist in history to make the Top 10 look like her tracklist.

Taylor Swift’s lyrics makes ‘all of us’ feel things

From academia to TV shows, Taylor Swift has been acknowledged as a genius lyric master and songwriter who just knows how to resonate with fans.

Some examples include:

Hi, It’s Me, I Am The Problem, It’s Me (Anti Hero, Midnights) or Don’t treat me like some situation that needs to be handled / I’m fine with my spite and my tears, and my beers and my candles, (Closure, from Evermore).

Taylor Swift can utter a thing or two about life seamlessly never shying away from being vulnerable and even sharing ‘shame’ of her own past with millions.

Speaking of her lyrics that delve deeper into her life, Taylor Swift was once candid in an interview.

She gushed: “I don’t think that art and suffering have to be holding hands. I think you can write songs about pain or grief … suffering … loss … hard things that you go through in life. Shame, you know, love to write about that one.”

But Tay Tay is not just about sharing her feelings, sometimes (well, too many times), she also makes music to clapback personal vendettas or simply stand up for herself. Not afraid of looking at the tabloid headlines crucifying her in the eye.

“Sometimes the lines in a song are lines you wish you could text-message somebody in real life,” Swift said in one interview. “I would just be constantly writing all these zingers — like, ‘Burn. That would really get her.'”

After all, she sings in Karma, Cause if you dare, you’ll see the glare/ Of everyone you burned just to get there/ It’s coming back around.

Got a long list of ex-lovers – Taylor Swift’s boyfriends

Taylor’s songs which talk a lot about her ex-lovers have been the center of media attention for two decades. The singer herself has even talked about the overly publicized attention her dating life gets. But there is no doubt that she truly dated a slew of Hollywood Heartthrobs.

Joe Jonas (2008)

Taylor dated the lead frontman of DNCE and former Jonas Brothers member, Sophie Turner‘s ex-husband Joe Jonas from July 2008 to October 2008. The breakup caught attention as Tay shared how Joe broke up with her in a 25-second phone call!

But there is no major Bad Blood there. However, fans claim Taylor Swift’s lyrics in Mr. Perfectly Fine is actually about the Sucker crooner. While she’s never come out herself to confirm it, Sophie Turner – before the Jonas divorce hit headlines – was even spotted wearing a friendship bracelet with it spelled out before the divorce.

So there’s that…

Taylor Lautner (2009)

Among the Lover crooner’s ex-boyfriends, Taylor Lautner has got the most love from fans as the singer wrote her heart-wrenching single Back To December for the Twilight star. Back then, we thought it was a double-Taylor match made in heaven with the movie star.

Lautner has also been supportive of the Daylight singer’s career over the years and that hasn’t stopped. Recently, he shared a TikTok about how he is having the post-Taylor Swift show depression after attending the Eras tour with his new wife (who is also called Taylor).

John Mayer (2009)

Taylor reportedly dated John Mayer when she was 19 and he was 32. The relationship was rocky, to say the least. Swifties claim her famous single Dear John is actually a recount of the relationship in the most Swift-esque manner possible.

Jake Gyllenhaal (2010-2011)

The Jake Gyllenhaal saga of Taylor’s life is best represented in her ten-minute record-breaking song All Too Well TV. With Jake, the Love Story singer also had a ten-year age gap which is supposedly one of the reasons for their relationship not working out.

Harry Styles (2012)

Among the list of top celebs that Taylor exchanged hearts with, Harry Styles is a fan favorite. The pair reportedly only dated for a month. But it doesn’t stop fans thinking Taylor Swift’s lyrics in Style is definitely about the One Direction member as the title quite clearly suggests it.

Calvin Harris (2015)

Calvin Harris dating rumors was well documented as they appeared for multiple award shows and public events together in 2015. But rumors say Harris broke up with the singer the next year.

I guess they were Never Ever Getting Back Together?

Tom Hiddleston (2016)

Tom Hiddleston and Taylor’s story rocked the Internet as the movie star was photographed in an ‘I Heart TS’ t-shirt vacay-ing with Tay Tay in 2016. Unfortunately, their romance was short-lived as the pair called it quits in the same year.

They were cute and Tom Hiddleston is such a nice man but deep inside this moment hurts after the lyrics:

“Pouring out my heart to a stranger, but I didn't pour the whiskey”

The meaning behind that line kills me, Im so sorry she ever felt that way😔

pic.twitter.com/YleYQ4ANcc

— 𝕄𝕪𝕝𝕒 🏳️‍🌈 (@hswift_) March 25, 2021

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Joe Alwyn (2017-2023)

Taylor’s longest love story was with none other than British star Joe Alwyn. While fans were sure that the pair would be each other’s end game, shock reports claimed the celebrity couple broke up earlier in 2023.

While Tay Tay and Joe mostly kept their relationship away from the camera, fans think she’s written a dozen songs about the relationship including Call It What You Want, Lover, Daylight, and more.

Joe has also collaborated with Tay in writing songs in her Pandemic albums, Folklore and Evermore, with the former credited as “William Bowery”.

Matt Healy (2023)

Followed by the big breakup, Taylor was linked to Matt Healy. Rumors exploded after the 1975 frontman was spotted attending Tay’s Eras tour. However, insiders claimed that the two casually hung out and it was never ‘that serious.’ That seemed to be the case when Matt Healy was seen making out with someone new this summer.

No hard feelings?

Who is Taylor Swift dating?

Travis Kelce (2023)

Taylor Swift and Travis Kelce dating rumors started swirling around after she attended a Kansas City Chiefs match. Later, the duo left on a ‘getaway car’ together, which couldn’t make it even more perfect.

Since then, Taylor has attended another Kansas City Chiefs match with her close friends including Blake Lively, Ryan Reynolds, Hugh Jackman, and Sophie Turner.

While the pair is yet to make it official, fans are already looking at their birth charts and swearing that they have an instant connection!

If you’re still unsure it’s written in the stars, check out every single word Travis Kelce has said about Taylor Swift if you don’t believe he’s smitten.

The history-making Eras tour

2023 has been a year to remember for Swifties. Not just because of Taylor’s topsy-turvy romantic life but for making history with her Eras tour.

Taylor Swift’s Eras Tour consists of 146 dates across five continents. It’s projected to “become the biggest in concert history, with the potential to gross over $1 billion.” Reports claimed that the US leg of the show had an average earning of grossly $13 million.

The Eras Tour started on March 17, 2023, in Glendale, United States, and is likely to conclude on November 23, 2024, in Toronto, Canada.

The Eras Tour Film – the Taylor Swift movie

While The Eras tour is well on its way to becoming the most successful concert tour, fans who can’t attend it will get to see a glimpse of all the action through Taylor Swift: The Eras Tour, the concert film. The world premiere is set for October 11, 2023, and will release in theaters worldwide on October 13, 2023.

The film has already made records as it earned $100 million in global pre-sales by October 5, becoming the most profitable concert film in history.

What’s next for Swifties?

Swifties are never running out of excitement, as after the Eras Tour concert film the singer will be releasing her re-recorded version of 1989 Taylor’s Version on October 27, 2023.

Once again, Taylor Swift fans will sing the lyrics:

Players gonna play, play, play, play, play
And the haters gonna hate, hate, hate, hate, hate (haters gonna hate)
Baby, I’m just gonna shake, shake, shake, shake, shake
I shake it off, I shake it off.

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Martina Birk

Update: 2024-07-30