Taylor Swift entered American royalty territory when she dated Conor Kennedy. Yes, we’re talking about the famous Kennedy family. Conor Kennedy is Robert F. Kennedy’s grandson, and the two were linked during the summer of 2012. The summer of 2012 was a glamorous one for Taylor.
She had befriended socialites Rory and Ethel Kennedy and spent a lot of time with them at their home in Hyannis Port, Massachusetts. Taylor even purchased some property in the area. Overall, the summer of 2012 seemed like a fun, laid-back one for Taylor. The relationship with Conor was a short summer fling. They were no longer seen together when September rolled around.
A Star Is Born
Taylor Alison Swift was born to Andrea and Scott Swift on December 13, 1989. Taylor spent her early childhood years growing up in Pennsylvania with her younger brother, Austin Swift. Her dad, Scott, was a stockbroker for Merrill Lynch, and her mom, Andrea, was a former marketing executive.
Looking back, Taylor’s immense fame and success seemed to be written in the stars. Her parents named her after the famous singer and writer James Taylor, who is one of the best-selling musicians of all time. Plus, Taylor’s grandmother, Marjorie Finlay, was a renowned opera singer and TV personality. All of these tidbits could be a coincidence. But, if you’re a Swiftie, you probably know that her rise to fame was meant to be.
She’s Always Been Drawn to Music
Taylor’s love of music started at a very young age. According to Britannica, Taylor began performing in school plays and children’s theater productions when she was in elementary school. But Taylor wasn’t satisfied with small-town theater productions. When she turned nine, her parents enrolled her in voice and acting lessons in New York City.
Once Taylor’s professional training began, her star began to rise. Her first gig was singing “The Star-Spangled Banner” at a Philadelphia 76ers game. Not bad for someone who was only eleven. As a preteen, she learned how to play the guitar. Following the examples of her idols, Shania Twain and Faith Hill, Taylor decided she wanted to pursue country music.
Welcome to Nashville
Nashville, Tennessee, is nicknamed “Music City” for a reason. It’s a cultural hub for country music. Everyone who’s anyone in country music usually congregates in Nashville to launch or grow their career. Naturally, Nashville is where Taylor Swift wanted to be. Thankfully, her parents were completely supportive of her dreams.
When Taylor was around 13 or 14, her parents sold their Pennsylvania property and moved to Hendersonville, which is a suburb near Nashville. Being closer to Nashville allowed Taylor and her parents to network, make connections, and break into the country music business. After a few years of networking and playing around Nashville, Taylor got her big break.
The Bluebird Cafe
Every Swiftie knows about The Bluebird Cafe. It’s a venue where many a country star has gotten their big break. Of course, Taylor Swift is one of those stars. She performed at The Bluebird Cafe in 2004 when she was only 14 years old. Her setlist included some covers as well as original songs that she had written herself.
Taylor’s stellar performance caught the eye of Scott Borchetta, a music executive who was about to launch his own independent label, Big Machine. Scott signed Taylor, changing the trajectory of her career forever. Both Taylor and Scott probably had no idea what was to come in the next few years.
Taylor’s First Record Deal
Taylor Swift was one of the first artists signed to Big Machine Records, with her dad investing in the fledgling company. Overall, it seemed like a pretty sweet deal, especially for Taylor’s budding career. Taylor quickly got to work on recording what would turn into her first album.
“Tim McGraw” was Taylor’s first single, released in June 2006 as a lead-up to her self-titled debut album. The song was co-written by Taylor and songwriter Liz Rose, but the concept was all Taylor. She came up with the idea for the song when she was only a freshman in high school. “Tim McGraw” was an immediate hit, spending a whopping 35 weeks on the “Billboard Hot Country Songs” chart.
The Real Story Behind “Tim McGraw”
Taylor Swift has always written her own songs. In fact, before she signed with Big Machine, she was signed with Sony/ATV to simply be a behind-the-scenes songwriter. It’s no surprise that Taylor’s debut single was all her own. She collaborated with Liz Rose during production, but the concept for the song originally came to Taylor while she was sitting in class at Hendersonville High School.
According to Taylor, a melody came to her while she was in math class, and the rest is history. The lyrics drew from real-life experience. She knew that her relationship with her boyfriend, who was a high school senior, was going to end when he graduated and went off to college. Taylor captured the sweet heartbreak that comes with losing someone at that age. Her lyrics have drawn people to her music from the very beginning.
“Taylor Swift” Debuts
On October 26, 2006, “Taylor Swift,” the self-titled debut album, came out into the world. And the world noticed. Taylor Swift’s debut album immediately created a buzz in the world of country music. Fans and critics alike praised Taylor’s music for the way it perfectly captured teenage heartbreak, love, and insecurity.
Taylor has a primary writing credit on every single song on the album. Obviously, people took notice because Taylor was only 16 at the time of the record’s release. Her masterful ability to write catchy country music and emotional lyrics at such a young age made her a force to be reckoned with.
The Opening Acts Begin
Every superstar has to start somewhere. Taylor Swift began with a bang. After the release of her debut album, she began promoting it with a fiery passion. Taylor and her team did a six-month radio tour to get her music on the airwaves. In an unorthodox move, Taylor also heavily promoted her music via MySpace. This was a stroke of marketing genius because she was able to reach a younger country music audience who was immediately receptive to her work.
What was even more impressive was Taylor’s opening act line-up. She toured with big names like Rascal Flatts, Brad Paisley, and George Strait. In a wonderful twist of fate, a young Taylor Swift also got to open for Tim McGraw and Faith Hill on their joint tour in 2007. We can only imagine how thrilling that must have been for her.
Taylor’s Crossover Begins
Taylor Swift’s first album was strictly country, but her sophomore album tried something different. “Fearless” came out on November 11, 2008, and catapulted T-Swift into the mainstream. The album stuck to her country music roots but also incorporated elements of pop.
The singles from “Fearless” put Taylor on the map. There’s a soft spot for songs like “You Belong With Me” and “Fifteen” in every Swiftie’s heart. These songs, plus “Love Story” and “White Horse,” became mainstream radio hits. “Fearless” was such a runaway hit that it’s now lauded as the most-awarded country album of all time. Oh, and Taylor was only 18 when she wrote a majority of the songs. No big deal.
The Taylor Swift Effect
Even if you’re not a fan of Taylor Swift’s music, there’s no denying that she is a talented songwriter. The young songstress garnered fans from the very beginning because of her candid lyrics about love, loss, friendship, and teenage yearning. Her sweet, emotional lyrics struck a chord with young people everywhere, particularly young women.
Taylor has never been afraid to write about her life experiences and the emotions that accompany them. Although she received some sexist criticism about her lyrics, many young people saw themselves and their own emotions reflected in Taylor’s songs. This raw emotion has been the key to her success from the very beginning.
An Enduring Relationship
While people love to obsess and speculate over who Taylor Swift is dating, there’s one relationship that has withstood the test of time. Taylor and Selena Gomez have an enduring friendship that hasn’t been broken by fame, men, or gossip. The two met when Taylor was dating Joe Jonas, and Selena was dating Nick Jonas.
According to Selena, the two immediately clicked when they met on a double date with the Jonases. While those romantic relationships didn’t last, their friendship has only grown stronger over the years. Thankfully, Selena and Taylor have been there for each other as their respective careers have grown, changed, and flourished.
Taylor & Joe
With Taylor’s rise to fame came a natural curiosity about who she was dating. Taylor and Joe were a headlining couple when they dated. No, we’re not talking about Joe Alwyn. He comes on the scene later. We’re talking about none other than Joe Jonas. The pair dated for a few months in 2008, much to the delight of fans everywhere. After all, the Jonas Brothers and Taylor Swift were two of the hottest musical acts of the early 2000s.
Alas, the romance did not last. Allegedly, Joe Jonas broke up with Taylor in one of the worst ways possible: over the phone. That’s almost as bad as texting a breakup message. To make matters worse, Taylor admitted on “The Ellen DeGeneres Show” that the phone call was under 30 seconds. Apparently, Jonas didn’t waste any time. Sheesh.
A “Fearless” Rebound
Many fans believe that the singer-songwriter wrote several songs allegedly inspired by her short-lived romance with Joe Jonas. Her sophomore album “Fearless” came out in November 2008, just a month after Joe broke things off with her. Fans immediately started scouring her new lyrics for clues about their doomed romance.
While many speculate that “Mr. Perfectly Fine” and “Better Than Revenge” might be about Joe, Taylor did confirm that “Forever & Always” was inspired by her relationship with the former Disney star. She told “The Ellen DeGeneres Show” that she squeezed in a last-minute recording session for the song right before “Fearless” was released. The relationship didn’t work out, but the song sure did.
“Ellen” Regrets
Taylor was just 18 when she and Joe broke up. Anyone who remembers being a teenager will vividly remember the hurt and saltiness that come along with a breakup. A young Taylor was pretty candid on “The Ellen DeGeneres Show” back in 2008. She threw a few salty jabs at Joe regarding the breakup.
Years later, Taylor came back on the show and voiced regret for throwing punches at Joe. She told Ellen in 2019 that putting Joe Jonas on blast was “too much.” The admission was during a game show-style segment, but you can totally tell that Taylor regrets her actions. It’s okay, Taylor. We’ve all been vengeful teenagers who love talking smack about our exes. We forgive you.
Her First Headlining Tour
The success of Taylor’s sophomore album allowed her to start her first headlining tour ever. The “Fearless Tour” kicked off in April 2009 and was a huge success. Much like the music-making process, young Taylor was very involved in aspects of the tour production.
She had input on the stage design and direction. Taylor wanted her audience to experience where she was and what she was going through when she wrote each song that she performed. The result was a rotating set that included a gorgeous castle backdrop. Unsurprisingly, Taylor’s tour was a success. Her tour tickets sold out in minutes, even back in 2009.
An On-Screen Romance
Taylor Swift was pretty young when she rose to fame, so it’s no surprise that she casually dated a few guys in the early 2000s. Remember the guy from her “You Belong With Me” music video? It turns out that Taylor’s on-screen romance with actor Lucas Till mirrored reality a little too closely.
The two casually dated for a few months in 2009. However, it was never anything serious. Lucas told “MTV” that they both really liked each other when they worked on “Hannah Montana: The Movie.” However, they quickly realized that they liked each other more as friends. The breakup was amicable, and there were no hard feelings.
The Two Taylors
The world found out that Taylor Swift was “Team Jacob” when she dated “Twilight” actor Taylor Lautner in the fall of 2009. The duo quickly became known as “Taylor Squared.” All things considered, it’s a pretty cute nickname. The two Taylors first met on the set of “Valentine’s Day,” where they played high school sweethearts.
Apparently, their on-screen chemistry translated to real life. The two stars played it coy, but paparazzi spotted them going out to dinner, hockey games, and other very date-like outings. Lautner famously presented Swift with a VMA for her music video “You Belong With Me” at the 2009 “MTV VMAs.” The two exchanged a tight hug, adding further fuel to the relationship fire.
That One VMA Moment
It’s a universally accepted fact that every Swiftie remembers where they were when they saw the 2009 “MTV Video Music Awards” debacle. Let’s take a walk down memory lane, shall we? Taylor Swift had just won her very first MTV VMA for Best Female Video. Her then-boyfriend, Taylor Lautner, presented her with this amazing achievement.
A young and excited Swift starts to give her enthusiastic acceptance speech. Seemingly out of nowhere, Kanye West appears onstage and takes the mic from Taylor, proclaiming that Beyoncé had one of the best videos of all time. A bereft and bewildered Taylor was left onstage, alone. Everyone watching thought it was a stunt at first, but the look on her face at the end made it clear that it definitely was not scripted.
“Kanyegate” Wasn’t Scripted
While the Video Music Awards are known for headline-making performances and scandalous stunts, the Kanye West-Taylor Swift debacle was completely unplanned. Taylor had no idea that Kanye was going to jump on the stage and indirectly accuse her of stealing the award from Queen Bey.
Tay’s then-boyfriend Taylor Lautner, who presented the award, later admitted that he had no idea what was going on. In 2023, Lautner explained the situation on his podcast, “The Squeeze.” As he was standing onstage in the background, he had no idea that the whole thing wasn’t a skit. Once Swift turned around and Lautner got a glimpse of her upset face, he quickly realized that something was very wrong.
The VMA Fallout
Despite the shocking VMA moment with Kanye West, Taylor still managed to have a stellar night back in 2009. After getting interrupted by Kanye onstage, she performed “You Belong With Me” on a moving subway car and a cab outside of Radio City Music Hall. Iconic. Later on in the night, Beyoncé won a VMA. But she didn’t want the limelight for herself.
With incredible kindness and grace, Beyoncé called Taylor back onto the stage so she could have her winning moment. No one was expecting this positive plot twist. We have a feeling that Beyoncé and Taylor Swift gained some new fans that night.
“Back to December”
Sadly, Taylor Squared wasn’t built to last. The couple allegedly broke up in December 2009 after a few months of dating. Although the tabloids tried to make it into a big deal, sources close to both stars said it wasn’t that big of a deal. The two liked each other and decided to split up because of their busy schedules.
Besides, Lautner lived in LA, and Swift lived in Nashville. Swifties got more information when “Back to December” was released on “Speak Now,” which came out in October 2010. The song’s lyrics make it pretty obvious that it’s about her relationship with Lautner. In another plot twist, her lyrics also imply that she was the one to break things off.
No Hard Feelings
Despite their much-publicized relationship and breakup, Taylor Squared never had any hard feelings toward each other. Neither of the Taylors ever spoke ill of each other to the press. In fact, Swift called Lautner one of her closest friends in a 2010 interview with “Glamour.”
Over the years, the two have maintained their friendship. Their relationship came full circle when Lautner starred in Taylor’s 2023 music video for “I Can See You.” The song and music video were part of the re-release of “Speak Now (Taylor’s Version).” Lautner even made a cameo appearance at Swift’s Eras Tour performance, where she announced the release of the album.
Taylor’s “Glee” Connection
The late Cory Monteith famously dated his “Glee” co-star Lea Michele up until his untimely death in 2013. Before that, Cory may have briefly dated Taylor Swift for a few months in 2010. Rumors swirled around the two when they were seen together at a bowling alley. From there on out, interviewers began questioning the two about their possible relationship.
There’s no hard evidence that Cory and Taylor ever dated. Some fans think Swift’s song “Mine” is about Cory, but she’s never confirmed the rumors. Maybe it was a secret romance, or maybe it was a fabrication by the tabloids. Whatever the case, the two always had nice things to say about each other when asked. Sadly, Cory passed away too soon in 2013.
“Speak Now” Debuts
By the time Taylor’s “Fearless” world tour was over, she was a solidified star. Her songs were all over the radio, and the paparazzi were weirdly obsessed with who she was dating. However, gaining fame at such a young age had a different side effect on Taylor. The critiques about her singing voice and doubts about her songwriting abilities stuck with her.
Taylor turned those critiques into motivation. She wrote the entirety of her third album, “Speak Now,” while she was on the road for “Fearless.” That’s right. Her hit album “Speak Now” with fan favorites like “Mine” and “Mean” was written solely by Taylor. She wanted to prove her critics wrong and establish herself as a bonafide songwriter in the industry. We have a feeling that she succeeded beyond her wildest dreams.
Enter: John Mayer
Okay, so why do most Swifties despise John Mayer? Well, let’s get into it. John Mayer and Taylor Swift were romantically linked from late 2009 into 2010. Although John and Taylor never “officially” confirmed their relationship, fans and tabloids alike were pretty certain there was a little something going on.
The pair were first linked when they recorded “Half of My Heart” together. The collaboration brought them together many times onstage. Plus, they always spoke highly of each other in interviews. The two were spotted a few times going out to dinner and the like. If they really were dating, the romance ended sometime in the first half of 2010.
“Dear John…”
No one really gave the alleged romance between Taylor Swift and John Mayer much thought. That is, until “Speak Now” came out in October 2010. Taylor’s song “Dear John” made it pretty obvious that something did, in fact, happen between the two. And it didn’t end well.
In “Dear John,” Taylor references an age gap (John was 32 when he supposedly dated a 19-year-old T-Swift) and withstanding “dark, twisted games.” Dang. John Mayer’s reaction to the song further confirmed their relationship. He got extremely defensive, calling Taylor’s approach “cheap songwriting.” Ouch. To this day, many Swifties have not forgiven John for his vengeful words.
She’ll Never Tell
Every new Taylor Swift album comes with brand-new speculation about who each song is about. Despite (or because of) the hundreds of theories floating around the internet, Taylor has never come out and explicitly named names. We may never know who “Dear John” is REALLY about, and that’s fine with Ms. Swift.
Taylor has spent most of her career reminding people that she never discloses who her songs are about. We can theorize and wildly speculate all we want, but Taylor may never tell us if we’re right or not. Honestly, the speculation is part of the fun. As long as fans don’t go after and harass any of her exes, analyzing her lyrics can be pretty entertaining.
A Relationship We Know “All Too Well”
Even the most casual of Taylor Swift fans can tell you all about her short-lived romance with Jake Gyllenhaal. After all, one of her favorite songs is rumored to be about him. Taylor and actor Jake Gyllenhaal were romantically linked over the span of three months in 2010. Much like the rumored romance with John Mayer, there was a sizable age gap between the two lovebirds. Taylor was 20 when she started dating the 29-year-old actor.
But how did the two famous stars meet? Well, through another super-famous person, of course. The two allegedly met for the first time at a dinner party hosted by Gwyneth Paltrow and her then-husband, Chris Martin. Sparks flew, and the couple was soon linked in the press.
The Public Catches On
We’ll probably never know when Taylor Swift and Jake Gyllenhaal officially started dating. But people knew something was up when the two were spotted filming “Saturday Night Live” together in October 2010. According to InStyle, sources who were backstage with the two stars said that they were extra-cautious about being seen too close together.
Is this the flimsiest evidence ever? Probably. But Swift fans loved every second of speculation. Who doesn’t love a cozy fall romance? Jake and Taylor were also spotted having brunch in New York City the same weekend as “Saturday Night Live.” If that’s not hard evidence, we don’t know what is.
“This Thing Was a Masterpiece”
Alas, the romance between Taylor Swift and Jake Gyllenhaal didn’t last. Rumors started swirling about a possible breakup around the holidays. Taylor spent New Year’s Eve in Nashville, while Jake was spotted ringing in 2011 in NYC. By early January, it was pretty evident that any possible romance was extinguished.
However, their breakup wasn’t the last that Jake Gyllenhaal would hear from Taylor Swift. As any Swiftie scholar knows, Taylor’s song “All Too Well” from her 2012 “Red” album is widely accepted to be about the “Donnie Darko” star. Of course, neither Taylor nor Jake has confirmed such rumors. But we Swifties know how to read between the lines.
“All Too Well” Context Clues
“All Too Well” is perhaps Swift’s most famous breakup song to date. Reading the lyrics, it’s pretty obvious to most Taylor fans that it’s about her ex, Jake Gyllenhaal. Many of the lyrics seem to reference a guy who sounds a lot like the famous actor. “You used to be a little kid with glasses” seems to be the most common clue that fans reference.
Plus, a line of the song references her budding romance taking place in the fall, which is exactly when Taylor and Jake dated. Why, oh why, does Taylor Swift torture us like this? We need answers! Regardless of whether “All Too Well” is about Jake Gyllenhaal or not, there’s no denying that it is a darn fine breakup song.
What’s Up With the Red Scarf?
Taylor Swift is famous for putting Easter eggs and clues into her song lyrics. When “All Too Well” came out in 2012, fans got to work. The internet immediately honed in on the line about leaving a red scarf “at your sister’s house.” What’s the meaning behind that? Well, fans needed to know. Naturally, they reached out to Maggie Gyllenhaal, Jake’s famous sister.
Maggie swears she has no idea what the red scarf is about. The topic came up on an episode of “Watch What Happens Live,” and Maggie was straightforward with host Andy Cohen. She told him that she had no idea what fans were talking about. Maggie then went on to say that it was completely within the realm of possibility that a red scarf was still at her house. Who knows?
She’s Dated a Kennedy
Taylor Swift entered American royalty territory when she dated Conor Kennedy. Yes, we’re talking about the famous Kennedy family. Conor Kennedy is Robert F. Kennedy’s grandson, and the two were linked during the summer of 2012. The summer of 2012 was a glamorous one for Taylor.
She had befriended socialites Rory and Ethel Kennedy and spent a lot of time with them at their home in Hyannis Port, Massachusetts. Taylor even purchased some property in the area. Overall, the summer of 2012 seemed like a fun, laid-back one for Taylor. The relationship with Conor was a short summer fling. They were no longer seen together when September rolled around.
Dating in Style
The Haylor era of Taylor’s dating history has spawned some of the best pop songs from both parties involved. In case you don’t remember, “Haylor” is the nickname bestowed on Taylor Swift and Harry Styles when they dated back in 2012-2013. Taylor and One Direction fans went wild when the two were photographed on a date at the Central Park Zoo.
Apparently, the two first met at the 2012 “Kid’s Choice Awards” in March 2012. Harry and Taylor were two of pop’s biggest stars, so fans immediately fell in love with the power couple. The two were spotted jetsetting to England, Park City, and New York for various adorable dates and getaways.
Haylor Comes to an End
As with many highly publicized relationships, the romance between Taylor and Harry Styles didn’t last for long. After going on a Caribbean vacation together, Taylor was spotted leaving by herself while Harry stayed behind. This immediately sparked breakup rumors, which were confirmed in January 2013.
Although fans were sad to see the power couple breakup, “People” reported that sources close to the stars said the relationship was never very serious. The pair were probably just having fun together and decided to split amicably. Besides, their schedules were extremely busy. They both had their whole careers ahead of them and decided to focus on that.
Taylor Dazzles at the MTV VMAs
We’ve seen Taylor’s style evolve throughout her career. 2013 was a pivotal year for her, especially in the style department. Taylor showed up to the 2013 “MTV Video Music Awards” wearing a stunning gown that showed the world she was just as mature and sultry as the best of them.
Her Hervé Léger by Max Azria gown featured a plunging neckline with a jewel-encrusted bodice that showed off more skin than was usual for the wholesome pop star. Wild success is usually Taylor’s preferred style of revenge, but many consider this stunning navy blue gown to be her “revenge dress” after her breakup with Harry Styles. Either way, she looked absolutely stunning.
Let the “1989” Speculation Begin
Taylor Swift’s “1989” record was a groundbreaking career move. It not only solidified her transition to pop, but it gave fans another opportunity to scour her lyrics and speculate about the subjects of her new songs. By the time of the album’s release, Taylor and Harry Styles had been broken up for over a year. That didn’t stop Swifties from finding the One Direction star in some of her songs.
To this day, many fans think “Out of the Woods” and “Style” are about her relationship with Harry. “Style” seems like a pretty spot-on reference, especially because the chorus references someone with a James Dean look in their eyes. If these songs are indeed about Harry, we’d like to thank him for the inspiration.
Two Can Play That Game
Taylor draws from her real-life experiences to write her songs. She’s not the only artist who draws inspiration from past relationships. Fans have noticed parallels and references between Taylor and her ex, Harry Styles, when it comes to their music. Harry has released some songs that play into the idea that they’re about his past relationship with Taylor.
For example, most fans are pretty convinced that “Two Ghosts” is about Taylor Swift. The lyrics of Harry’s song seem to play on Taylor’s “Style” lyrics. “Two Ghosts” includes lyrics about red lips and white shirts. Coincidence? We’ll let you be the judge.
A Brief DJ Era
Let’s be honest. Almost every girl has a misguided DJ era in their dating life, right? We’re not saying Taylor’s relationship with DJ and producer Calvin Harris was misguided, but even she isn’t immune to such an era. Taylor and Calvin were first introduced by their mutual friend, singer Ellie Goulding, at the “Elle” Style Awards in February 2015.
Taylor and Calvin were an item for a little over a year. From Calvin posting Instagram photos of Taylor’s cats to attending the “Billboard” Music Awards together, the two seemed to be having a great time together. They tried their best to keep their relationship out of the public eye, but that certainly failed when they officially broke up.
A Twitter Meltdown
Taylor and Calvin broke up in June 2016. Their breakup immediately became even more publicized than their actual relationship. The rumor mill became too much for Calvin, who ended up posting a multiple-tweet rant on his account. Apparently, Calvin snapped because he felt like the press was giving Taylor all the credit for their collaborative track “This Is What You Came For.”
In his series of now-deleted tweets, Calvin goes off on Taylor. He accuses his now-ex of stirring the pot because she was “off tour” and bored. For the record, Taylor Swift co-wrote the track with Calvin under the alias Nils Sjöberg. Overall, Calvin's Twitter breakdown was not a good look. He admitted to British GQ that he regretted his impulsive rant.
A “Famous” Feud
After his infamous 2009 “VMA” speech, Kanye West publicly apologized to Taylor Swift. Taylor Swift wrote a song about it and performed it at next year’s “VMAs.” Feud over, right? Well, that’s what we all thought until Kanye released “Famous” in 2016. The song features a line where Kanye asserts he made Taylor famous.
To add insult to injury, the music video featured a bunch of nude wax figures lying in bed next to each other. One of them looked uncannily like Taylor Swift lying next to Kanye. A public uproar ensued, with Taylor insisting that she never consented to being called out by Kanye in such a demeaning way. Kim Kardashian, Kanye’s wife at the time, publicly stated that Taylor was lying.
Kim K Strikes Back
In an unprecedented turn of events, Kim Kardashian released a video of a phone call between Taylor and Kanye. The phone call was recorded without Taylor’s knowledge or consent. In the phone call, Kanye is telling Taylor about his upcoming single, “Famous.” Taylor is polite on the call, but it’s pretty obvious that she doesn’t know she’s being recorded, much less on speaker.
Kim said she released the footage to prove that Taylor was completely aware of how she would be featured in the song and video. While Kim probably thought this move was strategic, it left a bad taste in the public’s mouth. Taylor shot back by saying that she never heard a final version of the song. She then went on to say that she wanted to be excluded from the narrative of this scandal.
Taylor’s Grammy Acceptance Speech
Taylor’s “1989” won a Grammy for “Album of the Year” in 2016. This win made Taylor the first female artist to win the award twice, which is a pretty big deal. Taylor knew the significance of her victory, and she included a little jab at Kanye and Kim in her acceptance speech.
While onstage, she addressed all of the young women watching at home. “There are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame,” she said. Hmm... We wonder who she’s talking about…
“Hiddleswift” Is Born
Amidst the dramatic feuding and stressful press, Taylor had a whirlwind romance with actor Tom Hiddleston. Like many of Taylor’s shorter-lived relationships, the two stars dated for about three months after sharing a dance at that year’s Met Gala.
Rumors immediately began swirling that the relationship was a PR stunt, but Tom went on the record with GQ in 2017 to say it was the real deal. The duo had a ton of fun together over the summer of 2016. Tom was even photographed wearing an “I Heart T.S.” shirt while attending Taylor’s annual 4th of July bash at her beach house. Although they broke up when summer was over, it appeared amicable.
A Year Away From the Cameras
We didn’t see much of Taylor Swift in 2017. After her much-publicized relationships with Calvin Harris and Tom Hiddleston, her feud with Kimye, and her “1989” promo, Taylor consciously chose to disappear from the spotlight. The move was unprecedented because Taylor had never taken such a long break in her career.
Her reclusiveness was so complete that the public truly didn’t know where she was. There were no paparazzi sightings in New York, no tours, and no news of new relationships or music. In a 2023 interview with “Time,” Taylor revealed that 2017 was a very challenging time for her. She felt as if she had been over-exposed and canceled after the Kanye controversy, so she decided to step back and recoup.
A Low-Key Romance
There could have been another reason we didn’t see much of Taylor Swift in 2017. Rumors began swirling that Taylor was dating British actor Joe Alwyn. The two kept things extremely private, with no public outings or admissions to the press. Despite the secretive couple never making their relationship publicly official, Swifties were able to pick up on some clues.
The first clue was Taylor and her friends attending the premiere of Joe’s movie “Billy Lynn’s Long Halftime Walk” in 2016. It’s not even clear if Joe was there, but Taylor’s presence was a pretty big clue. Joe and Taylor were spotted by paparazzi throughout 2017. Notably, they were spotted together in Nashville, New York, and at an Ed Sheeran concert.
A Reputation-Changing Album
Call it what you want, but “Reputation” was definitely a revenge album. The album that Taylor mysteriously worked on during her hiatus debuted in November of 2017. Fans went wild over her new look and sound. They heard an anger and rage that they had never heard from Taylor before, especially on tracks like “Look What You Made Me Do.”
“Reputation” marked a point in Taylor’s career where she was trying to rebuild her reputation after the public and demeaning feud with Kim and Kanye. It was a public comeback that fans went wild for, especially when the “LWYMMD” music video premiered and garnered 43.2 million views on its first day.
A Different Approach to Press
Taylor Swift was still recovering from a difficult few years. For this reason, many people believe Taylor didn’t do any press for “Reputation” when it came out. She wanted the work to speak for itself instead of doing a nonstop press tour. She did drop a few Easter eggs for fans, though.
According to Elle, Taylor Swift told fans at a secret listening party that “Gorgeous” was most definitely about her low-key boyfriend, Joe Alwyn. That didn’t stop people from reading between the lines and theorizing about other songs, though. Some Swifties have speculated that “Dress” is about when she met Joe for the first time at the Met Gala in 2016.
Joe and Taylor Make It Instagram Official
You know things are serious when a couple decides to make their relationship Instagram official. Taylor and Joe did just that in 2018. Well, kind of. Fans freaked when they posted separate photos of themselves standing next to the same cactus.
Joe posted his photo the day after Taylor’s with an elusive cactus emoji. The coordinating photos made it pretty obvious that the two were spending plenty of time together. Other than that, the two remained mum about their relationship. Whenever Joe was asked to comment, he would gracefully steer the interview back to his work as an actor.
A Glam After-Party
Taylor ditched the 2019 Grammy Awards in favor of a fun BAFTA Film Awards after-party with Joe Alwyn. Joe attended the BAFTA Film Awards ceremony solo in celebration of his film “The Favourite” and linked up with Taylor afterward. Fans loved this moment because, even though the two were notoriously private, Taylor wanted to show her support.
Taylor wore a stunning pale blue Stella McCartney gown with a coordinated trench coat to the party. Although there are few photos of the two together at the event, attendees said they sat at the same table and were obviously together. In a sly nod to Joe, Taylor posted a photo of her BAFTA dress with a caption referencing “The Favourite.”
The Big Machine Masters Fiasco
Although Taylor seemed happy and fulfilled in her personal life, she faced yet another hurdle in her professional life in 2019. Taylor had moved on from Big Machine Records to Republic Records in 2018. However, she came to blows with her first record label when founder Scott Borchetta sold the company to Scooter Braun of Ithaca Holdings.
So, what was the big deal? Well, Taylor posted an explosive Tumblr announcement stating that Big Machine didn’t give her a fair opportunity to buy back the masters of her first six studio albums. Apparently, she had been trying to do so for years. Scooter was the new owner of her original masters, meaning he could license and profit from them at will. The dispute sparked an industry-wide debate about artist’s rights.
Shots Fired
The floodgates opened once Taylor posted her explosive Tumblr accusations against Scooter Braun and Scott Borchetta. Many speculate that Taylor was especially upset about her master going to Scooter Braun because he was a former manager of Kanye West. We all remember the intense and very public feud between the two artists, right?
Taylor accused Scooter of being a bully in the industry. She threw further accusations against Big Machine by stating the label prevented her from using the rights to her own music during the 2019 “American Music Awards” and in her “Miss Americana” documentary. In the end, Taylor was not able to wrestle the ownership of her music out of Scooter’s hands. But, as any Swiftie knows, she found her own way to strike back.
A Not So Cruel Summer
Taylor Swift released “Lover,” her seventh studio album, on August 23, 2019. This album marked a significant moment in her career. “Lover” was her first album released under Republic Records, not Big Machine Records. That meant “Lover” was the first album in which Taylor owned all the master recordings.
“Lover” was a special album to Taylor and her fans because it was the first record where Taylor felt like she had total creative freedom. The album was a complete transformation from her “Reputation” era. She used pastel aesthetics and bubblegum pop imagery to talk about love, LGBTQ+ rights, and so much more.
But Where’s Joe?
Okay, so which “Lover” songs are about Joe Alwyn? That’s what many Swifties wanted to know the moment Taylor’s album dropped in 2019. Naturally, the internet immediately began dissecting lyrics and speculating. “Paper Rings” and “Lover” seem to be the most obvious ones, but there might be Easter eggs in other songs.
Taylor makes plenty of references to the color blue, which Swifties believe represents Joe. In all honesty, pretty much every song on the “Lover” album has a line or two that can be associated with Joe if you look hard enough. From those sexy lines in “Cruel Summer” to the heartbreaking ones in “Cornelia Street,” everything is open to interpretation.
Taylor Becomes Her Favorite Animal
We all know that Taylor loves her cats more than anything in the world. Who better to star in the on-screen production of the famous Broadway musical “Cats,” then? Taylor was cast as Bombalurina in the strange on-screen adaptation. Everyone knows that Taylor has been trying to break into the movie biz for quite some time. Alas, “Cats” was not her breakout role.
The movie was a huge flop, with fans and critics alike calling it “unhinged.” Taylor’s role was much smaller than originally anticipated. In fact, it was more like a hyped-up cameo. She only has one line! Despite the weird digital fur and the overall box office disappointment, Taylor has no regrets about her role in “Cats.” She later revealed that she had a blast on set and didn’t care if people thought the movie was weird.
“Miss Americana” Debuts
Taylor Swift’s life has been well-documented by the press since she was a teenager. “Miss Americana” was Taylor’s chance to set the record straight and show fans a different, more raw side of herself. The documentary debuted on Netflix in January 2020 and was an immediate hit.
In “Miss Americana,” director Lana Wilson followed Taylor as she finished her Reputation tour in 2018 and worked on releasing her album “Lover” in 2019. Home videos and candid moments are sprinkled throughout the film, giving Taylor a chance to control her narrative in a way she couldn’t before. Overall, “Miss Americana” was viewed by fans as an insightful, if somewhat produced, peek into the famous singer’s life.
A Rare Swift-Alwyn Appearance
Throughout the course of their relationship, Taylor Swift and Joe Alwyn never walked a red carpet together. However, the 2020 Golden Globes marked a pretty public appearance for the private couple. They didn’t walk the red carpet together, but they publicly sat together during the award ceremony.
Taylor Swift still has her red carpet moment. She showed up solo in a stunning yellow and blue gown by Etro. The floor-length gown featured larger-than-life florals and a stunning train. The singer was nominated for her song “Beautiful Ghosts” in the 2019 film “Cats.” Although she didn’t take home any awards that night, she and Joe had a blast at the after-party together.
Who Is William Bowery?
When Taylor dropped her surprise album “Folklore,” she posted a heartfelt message on her Instagram thanking her collaborators. She failed to tag one person in her caption: a so-called “William Bowery.” This mystery man supposedly co-wrote two songs on “folklore,” and Swifties began investigating his true identity.
Thankfully, fans didn’t have to speculate on William Bowery for too long. Taylor confirmed that Bowery was, in fact, Joe Alwyn. Joe’s involvement in “folklore” was revealed in the “Disney+” film about the record. Taylor shared that she and Joe decided to collaborate for the first time on the songs “Betty” and “Exile.” They were nervous about working together professionally, but we’re glad they did.
A Prolific 2020
The world changed in an instant for many people in 2020, including Taylor Swift. In the midst of a global shift, the prolific songwriter and singer released not one but two brand-new albums. Both “Folklore” and “Evermore” were released in 2020, within five months of each other. Fans went wild.
Both “Folklore” and “Evermore” are more folksy than Taylor’s previous albums. There was even a song collab with folk icon Bon Iver. Both albums were positively received by fans and critics, ranking on “best album” lists far and wide in 2020. “Folklore” won “Album of the Year” at the 2020 Grammys, and “Evermore” was nominated for the same category in 2022. Not bad for two albums that were produced remotely.
A Music Career (Taylor’s Version)
Taylor was feeling pretty defeated after Scooter Braun and Ithaca Holdings took ownership of her first six studio albums. In a 2023 interview with “Time,” Taylor recalls feeling completely devastated and defeated. Thankfully, she wasn’t down for long. Like a phoenix rising from the ashes, Taylor decided to strike back.
Taylor told “Time” that friend and fellow pop star Kelly Clarkson repeatedly told her to simply re-record her original albums. That’s how Taylor’s now-famous re-release albums were born. In an act of reclamation, “Fearless (Taylor's Version)” was released in April 2021. Although the first week of sales didn’t out-sell the original “Fearless” album, “Taylor’s Version” belonged entirely to the artist and no one else.
The BRIT Awards “Global Icon Award”
Taylor Swift just keeps the hits coming. In May 2021, Taylor became the first woman to win the BRIT Awards’ “Global Icon” title. That’s not all. Taylor also became the youngest artist and the first non-English singer to win the prestigious award. The award commemorates artists who have greatly impacted the music industry with their impressive achievements.
Taylor looked stunning in a two-piece Miu Miu outfit as she accepted the colorful award statue. Her inspiring speech included some familiar names like Jack Antonoff and a cute call-out to Joe Alwyn. In classic Taylor style, she profusely thanked her fans and provided motivation to artists everywhere to keep on going in the face of resistance.
Taylor Swift Surpasses a Childhood Idol
Taylor Swift has often cited country singer Shania Twain as a major source of inspiration. She grew up listening to Shania’s music and was inspired to pursue a career in country music because of her. Taylor must find it surreal to know that her childhood hero knows who she is. Even more so, breaking the records set by your idols must be wild.
In January 2022, Taylor Swift broke Shania Twain’s record for female artist with the most weeks at #1 on the “Billboard Country Albums” chart. Shania had previously set the record at 97 weeks. Taylor surpassed that record with a 98-week streak. Ever the generous artist, Shania was thrilled for Taylor. She tweeted out a congratulatory message, saying that records are made to be broken by new generations. Isn’t Shania the best?
Dr. Taylor Swift
In addition to all of her artistic achievements, Taylor Swift added an academic title to her resume. New York University awarded the pop singer with an honorary doctorate in 2022. Swift received her honorary doctorate from the prestigious university because of her prolific career and amazing achievements.
To celebrate, Taylor Swift attended NYU’s graduation ceremony and delivered the commencement speech. In her speech, she reminded the Class of 2022 to embrace mistakes, missteps, and the mess that is life. She acknowledged that even through life’s hardships, it’s important to learn, recover, and move forward. We know all too well that wiser words have never been spoken.
Fans Will Never Forget the Jake Gyllenhaal Era
When “Red (Taylor’s Version)” came out in late 2021, Taylor included a famous 10-minute version of “All Too Well.” This song was already a fan favorite, but the new extended version from the Vault made people go wild. Swifties even started harassing Jake Gyllenhaal, even though his relationship with Swift ended over a decade before.
The media attention and speculation got so out of control that he addressed it in a 2022 interview with “Esquire.” Although he said that the media attention from Swifties hadn’t affected his life, he also defended himself. He insisted that “All Too Well” was not about him, but Taylor Swift had every right to express herself and reflect on past experiences. Fandoms can certainly exhibit harassing behavior, so many people were thankful that Jake brought the topic up.
Taylor’s a Girl’s Girl
If anyone has any doubts about Taylor Swift being a girl’s girl, just point them to her friendship with Sophie Turner. Sophie married Taylor’s ex in 2019, but Joe officially filed for divorce in September 2023. There was a huge buzz around the separation, with many people speculating that Joe was in the wrong.
Taylor made her stance pretty clear without having to say a word. She’s been friends with the former “Game of Thrones” star for years, but the two have gotten closer after Sophie and Joe’s separation. The two women have been seen going out to dinner, and sources say that Sophie was staying at Swift’s New York apartment amid the high-profile divorce. Bye, Joe.
A Record-Breaking World Tour
On March 17, 2023, Taylor Swift embarked on perhaps the biggest tour of her career. “The Eras Tour” kicked off in Glendale, Arizona, in a stadium full of 70,000 people. The tour was no joke, with Taylor undergoing intensive training up to six months before opening night. “The Eras Tour” quickly became Taylor’s most financially successful tour of her career thus far.
In fact, experts predict that “Eras” is set to be the highest-grossing stadium tour in US history, with an estimated revenue of over $2 billion. The tour is a genius production, taking fans through a retrospective of Taylor’s “eras,” including “1989,” “Speak Now,” and “Evermore.” With its elaborate stage production and gorgeous era-specific costumes, it’s no wonder this tour has captured the hearts and wallets of millions.
Taylor Swift IS the Economy
Even if you’re not a Swiftie, you undoubtedly heard about “The Eras Tour” in 2023 and 2024. Taylor’s 3.5-hour-long show is an artistic feat, but it also made headlines for its economic appeal. Economists immediately started noticing the boost in local economies whenever Taylor Swift came to town.
According to “Forbes,” Taylors “Eras Tour” generated almost $5 billion in consumer spending. That statistic is just for the United States. Just think about it. The tens of thousands of people attending Taylor’s concerts all spend money on tickets, travel, hotel rooms, dinner, merch, and so much more. Taylor’s 2023 tour, alongside Beyoncé’s “Renaissance” tour, stimulated the post-pandemic economy in a much-needed way.
End of an Era
Amidst the excitement for Taylor’s “Eras Tour,” fans wondered if her long-term boyfriend, Joe Alwyn, would make an appearance at any of her concerts. In March 2023, “People” reported that Joe would try to make it out to some of her shows. However, fans noticed that Joe was absent from every single concert.
Just a month into her tour, news broke that she and Joe had quietly broken up a few weeks prior. Fans were understandably heartbroken for Taylor and Joe, as they seemed like a solid couple. Sources close to both Taylor and Joe told news outlets that the breakup was amicable. The two simply grew apart after facing conflicts surrounding Tay’s level of fame.
In Her “Reputation” Era
After months of working tirelessly on her “Eras Tour,” Taylor enjoyed a night out at the 2023 “MTV Video Music Awards.” Fans were gobsmacked by her outfit choice for the award show because it brought her “Reputation” era to mind. She absolutely rocked a custom-made black Versace gown and strappy stiletto heels.
The Versace gown featured an asymmetrical line of gold buttons and a dangerously high leg slit. The low-cut neckline was balanced out by the gown’s asymmetrical straps. Taylor finished off her look with a smokey eye, a messy updo, and dark nail polish. If this doesn’t scream “Reputation,” we don’t know what does.
A “Collaboration” With The 1975
With news spreading of Taylor and Joe’s breakup, the paparazzi started noticing something. In the midst of her tour, Taylor was spending a lot of time with Matt Healy, the frontman of the band The 1975. Rumors started swirling that the two were casually dating, which sent Taylor and The 1975 fans into a tailspin.
The relationship was reportedly a “no strings attached” type of deal, but there was a degree of backlash. People started critiquing Taylor’s rebound choice because of problematic things Healy had said in the past. Some rude comments he made about rapper Ice Spice on a podcast especially caused outrage. Alas, the two stopped spending time together after about a month. Perhaps the heat was too much for Taylor.
The Boy on the Football Team
In the midst of her record-breaking “Eras Tour,” Taylor Swift made headlines for something else entirely. Brains broke, and fans freaked out when Taylor began dating Travis Kelce, the Kansas City Chiefs’ tight end. It all began when Travis mentioned attending the “Eras Tour” on his podcast in July 2023.
Taylor’s team took notice and put them in contact with each other. Rumors started swirling that the two were quietly seeing each other and secretly meeting up for casual dates in New York City. Kelce explained to the “WSJ Magazine” that someone from Team Swift heard his podcast episode and urged Taylor to get in touch with him. They were chatting for a few weeks prior to meeting in real life, so Kelce knew they’d get along without a hitch.
It All Started With a Friendship Bracelet
It turns out that Travis Kelce was more than just a casual fan. Travis dished the deets to his “New Heights” podcast cohost (and brother), Jason Kelce. According to Travis, he had made a special friendship bracelet just for Taylor Swift. What was so special about it? It had his number on it!
Sadly, Taylor didn’t have time to personally meet with Travis before or after the show. He was a little salty that he didn’t get to hand off his friendship bracelet, so he aired his grievances on “New Heights.” Thank Cupid Travis decided to talk about his “Eras Tour” experience on his podcast. Taylor’s team took notice, and the rest is history.
Taylor’s First Chiefs Game
September 24, 2023, is a date that Swifties will remember for many years to come. That date marked the first time Taylor Swift and Travis Kelce solidified all the dating rumors. Taylor was spotted at a Chiefs game with Travis’s mom, Donna. Not only was Taylor showing public support for Travis, but she was apparently charming his mom, as well!
Football fans and Swifties alike lost their minds when social media channels began posting pics and videos of the pop star on the sidelines. Tay and Travis left the game together and grabbed dinner – their very first public date. The couple was then photographed in a very public convertible car getaway. Whether it was a planned photo-op is irrelevant. Fans were freaking out.
The New Romantics
Any gal would be lucky to be in Taylor Swift’s inner circle, a.k .a. her squad. Once her relationship with Travis went public, Taylor started going out with a new group of friends. Taylor started going out on regular girl’s nights with the likes of Sophie Turner, her BFF Blake Lively, and famous football wife Brittany Mahomes.
From there on out, Taylor has been spotted with her new besties in the Chiefs box seats and at post-game after parties. Some people might have a problem with people tuning into NFL games for a glimpse of Taylor and her famous friends, but can you blame anyone? It’s all in good fun.
“Taylor Swift: The Eras Tour” Movie Premiere
Taylor Swift once again set a new precedent by releasing her iconic “Eras Tour” exclusively in AMC theaters. The film premiered on October 11, 2023, at The Grove in Los Angeles. Some lucky fans were even able to watch and sing along to the movie with Taylor herself in the theater with them.
The biggest surprise of the night was a very special guest. Beyoncé made a rare appearance at the premiere, with plenty of social media photo-ops of the two surfacing as the night went on. Beyoncé’s endorsement of the “Eras Tour” movie just made the night all the more spectacular for Taylor and fans alike. The media loves to pit famous female stars against each other, but Beyoncé’s appearance at Taylor’s premiere stifled all of that mean-spirited gossip.
“Traylor” Crashes “Saturday Night Live”
Things picked up for Taylor and Travis after the hard launch of their relationship. Overall, the vibe is that the two of them are having fun. They love dropping Easter eggs for their fans, such as their surprise cameos on “Saturday Night Live” in October 2023. The couple dropped by “SNL” after a romantic dinner at Nobu and decided to give the camera some love.
Taylor gave a surprise introduction for Ice Spice, and Travis made fans gasp when he appeared in a parody sketch about the insane “Traylor” coverage by sports channels. The happy couple then attended an “SNL” after-party until the wee hours of the morning. Talk about a whirlwind romance.
Breaking “Billboard” Awards
What record or glass ceiling hasn’t Taylor Swift broken? The “Cruel Summer” singer once again set a new record when the “Billboard Music Awards” rolled around in late 2023. She was nominated in a whopping 20 award categories and went home with 10 BBMA awards that evening.
Her ten wins in 2023 brought her BBMA count up to 39, making her tied with none other than Drake. Taylor didn’t attend the “Billboard Music Awards” because she was in South America for her “Eras Tour.” However, she made a pre-recorded acceptance speech where she thanked her fans for their support over the years.
Taylor and Travis Celebrate New Year’s Eve
Taylor and Travis have kept their relationship going strong during the media frenzy. The two lovebirds spent New Year’s Eve together, with Taylor attending a Kansas City Chiefs game against the Cincinnati Bengals. Taylor was spotted in the box seats wearing a cute letterman jacket to support Travis.
After the game, the couple rang in 2024 together at a small party. Photos and videos surfaced showing Taylor in a gorgeous bejeweled dress and her signature red lips. Travis wore a creative maroon suit. It looks like the couple had a blast at the intimate New Year’s Eve party, further endearing their romance to fans.
Taylor Swift: Person of the Century
It came as no surprise when “Time” announced Taylor Swift as their “Person of the Year” in 2023. The magazine featured three different covers of the star. The most memorable and charming one was Taylor posing in a black leotard with her beloved ragdoll cat, Benjamin Button.
In the “Time” article, Taylor discusses her rise to fame, her relationship with Travis Kelce, and the intensive training routine she undertook for the “Eras Tour.” To the delight of fans, she also divulged that she was recording “Reputation” vault tracks. “I’m very careful to be grateful every second that I get to be doing this at this level because I’ve had it taken away from me before,” Taylor told “Time.”
In Our Taylor Swift Era
Taylor’s recent “Eras Tour” is an exploration of the singer’s past career eras. However, there’s no denying that the entire world is in its Taylor era at the moment. Taylor Swift is more than just a pop singer. She is a cultural powerhouse who has changed the music industry and influenced the economy in countless ways.
Over the course of her career, Taylor has proven herself as a master storyteller and a savvy businesswoman who constantly reinvents herself. From boosting local economies with her tour to breaking revenue records, she’s a star who can’t be stopped. There have even been college courses written about her! We have no idea what Taylor Swift has in store next, but we do know that we’re ready for it.