The Many Exes of Taylor Swift and What They Have to Say About Her

Despite being tagged as a serial dater, Taylor Swift challenges this perception as “deeply sexist.” While she’s guarded about her relationships, her music often reveals glimpses of her romantic journey. From serious partnerships to casual flings, Swift’s past is a tapestry of love and heartache. Though fans may think they know it all, there are still surprises waiting to be discovered in the depths of her dating history. From high school boyfriends to her long-term relationships, here is everything you need to know about Taylor Swift’s dating history!

Brandon Borello: The Beginning

Her age: High School

Duration of Relationship: Unknown

In the bustling city of Nashville, where guitars echoed through the streets and dreams were born and shattered every day, Taylor Swift and Brandon Borello found themselves caught in the whirlwind of young love.

Their story began not with magic but with the typical awkwardness of high school. Taylor, with her wide eyes and dreams of stardom, caught Brandon’s attention in the crowded hallways. They were just two kids, drawn together by hormones and curiosity.

Their Relationship

Their relationship unfolded like any other teenage romance—filled with laughter, late-night conversations, and the occasional argument over trivial matters. It is rumored that Taylor wrote three songs about Borello, “Tim McGraw,” “Our Song,” and “Fifteen.”

But as they grew older, the cracks began to show. Taylor’s career took off, pulling her in different directions while Brandon stayed behind, struggling to find his own path. The distance strained their relationship, exposing the fault lines they had ignored in their youth.

How It Ended

Their breakup wasn’t a grand melodrama but a slow unraveling of two people who had simply grown apart. There were tears, of course, and moments of regret, but mostly, there was a quiet acceptance that their time together had run its course.

In the end, Taylor Swift and Brandon Borello parted ways like countless other couples before them—no fairy tale endings or grand gestures, just two people trying to find their way in the world, even if it meant doing so apart.

Sam Armstrong: The Beginning

Her Age: High School

Duration of Relationship: Unknown

It wouldn’t be high school without a few love triangles, would it? In high school, Taylor Swift found herself drawn to Sam Armstrong, a fellow musician with a quiet charm and an easy smile. Their relationship didn’t begin with fireworks and fairy tale magic but with a shared love for music and a mutual respect for each other’s talents.

As they spent more time together, Taylor and Sam discovered a deep connection rooted in their shared experiences as aspiring artists navigating the highs and lows of the music industry. They bonded over late-night jam sessions, swapping stories of triumphs and setbacks.

Their Relationship

Their relationship was far from perfect, marked by the same ups and downs that many couples face. They had their disagreements and misunderstandings, moments of doubt and insecurity. One of Taylor’s songs, “Should’ve Said No,” is rumored to be about Armstrong and his unfaithfulness.

But when you’re in high school, how deep can your connections really be anyway? Well, apparently, Sam Armstrong couldn’t handle having a connection with one of the world’s most adored women. All good things have to come to an end, and you will be shocked by how this union ended…

How it Ended

Like many high school relationships, things will seem to fizzle out at one point or another… And that was no different for Sam and Taylor. Sure, they had fun while it lasted, but apart from that, the two of them didn’t have too much in common at the end of the day.

And when all you hear is that Armstrong was potentially unfaithful during their short romance, you tend to think that Swift was better off from the start. Seeing as she is probably one of the most famous people in the world today, we have a feeling Armstrong regrets having treated her so badly.

Joe Jonas: The Beginning

Her Age: 18

Duration of Relationship: July 2008 – October 2008

Taylor Swift and Joe Jonas’s relationship was a whirlwind journey that captured the attention of fans and media alike. Their love story began in July 2008 amidst the glitz and glamour of Hollywood. Both rising stars in the music industry were introduced through mutual friends and hit it off almost instantly.

Their relationship was marked by public appearances, romantic gestures, and sweet moments captured by paparazzi cameras. They seemed like the perfect match—a power couple with talent, charisma, and chemistry to spare. However, behind the scenes, their romance faced its fair share of challenges.

Their Relationship

As two busy individuals navigating demanding careers, Taylor and Joe struggled to find time for each other amidst their hectic schedules. Long-distance and conflicting commitments often put a strain on their relationship, leading to tensions and disagreements.

Seeing as both parties in the relationship were focusing on their own careers, there wasn’t much space to work on their relationship… Some people say that Joe was definitely the one in the wrong, but Taylor wasn’t perfect throughout their relationship either. What happened next shocked everyone…

How it Ended

Taylor and Joe parted ways a few months later in October, amidst rumors of infidelity and heartbreak. While the details of their split remain largely private, Taylor later revealed that Joe had broken up with her over the phone in a brief call that lasted only 27 seconds…

With songs like “Forever and Always” and “Better Than Revenge,” Taylor made it clear that their breakup was far from amicable. However, Joe took to his MySpace account in 2008 to clear the rumors, “For those who have expressed concern over the ’27-second’ phone call … I called to discuss feelings with the other person. Those feelings were obviously not well-received. I did not end the conversation,” he wrote. “Someone else did. Phone calls can only last as long as the person on the other end of the line is willing to talk. A phone call can be pretty short when someone else ends the call.”

Lucas Till: The Beginning

Her Age: 19

Duration of Relationship: March 2009 – April 2009

The romance between Taylor Swift and Lucas Till was a brief but significant chapter in both of their lives, marked by the excitement of young love and the realities of fame. Their relationship reportedly blossomed in 2009 after Lucas starred alongside Taylor in her music video for “You Belong with Me.”

Their connection seemed genuine, fueled by shared interests and mutual admiration. Lucas, a rising star in Hollywood, and Taylor, a chart-topping singer-songwriter, found common ground in their passion for their craft and their desire to make a mark on the world.

Their Relationship

However, their romance faced the same challenges as any other young couple in the spotlight. Busy schedules, constant scrutiny from the media, and the pressures of fame put a strain on their relationship. Despite their best efforts to maintain a sense of normalcy, the demands of their respective careers often took precedence over their personal lives.

Seeing as their relationship was for such a short period of time; it is no secret that the pair weren’t able to make it work. Whether they were too young, too busy, or too unwilling to make things work, this couple didn’t stand the test of time. But there was always one very intriguing thing about Till and Swift’s connection…

How it Ended

You might remember the feud between Kanye West and Taylor Swift back at the 2009 MTV VMAs. Swift had just won the Video of the Year at the awards when West stormed on stage, stating that Beyonce was more deserving of the award as it was the year of “Single Ladies.”

Well, it was for the video clip of “You Belong With Me,” which starred none other than Lucas Till. Despite the end of their romance, Taylor and Lucas have both moved on with their lives, finding success and happiness in their respective endeavors. Their brief fling will always remind us of the “You Belong With Me” video clip, and honestly, that’s enough for us.

Taylor Lautner: The Beginning

Her Age: 19

Duration of Relationship: August 2009 – December 2009

When it comes to Taylor Swift and Taylor Lautner’s relationship, everyone can remember what a whirlwind romance it was. Their love story began on the set of the romantic comedy Valentine’s Day, where they played an on-screen couple.

Their off-screen chemistry was undeniable, and rumors of a real-life romance quickly began to swirl. They were spotted out and about together, attending events and enjoying each other’s company, fueling speculation about their budding relationship.

Their Relationship

As two of Hollywood’s hottest young stars, Taylor Squared, as they were affectionately dubbed by fans, seemed like the perfect match. But when her 2009 album “Speak Now” was released, fans had suspicions about the song “Back to December,” which was later confirmed to be about Lautner.

However, like many young couples in the spotlight, Taylor and Taylor faced challenges in their relationship. Their hectic schedules often kept them apart for long periods, and the pressures of fame added an extra layer of complexity to their romance.

How it Ended

Despite their efforts to make it work, the strain of their demanding careers ultimately took its toll on their relationship. In December 2009, just a few months after they were first linked together, Taylor and Taylor announced their breakup.

Details about the reasons behind their split remain largely private, with both Taylors choosing to keep the specifics of their breakup out of the public eye. However, in 2023, Swift and Lautner surprised fans everywhere with Lautner’s appearance in her song “I Can See You,” which appeared in her re-recorded album “Speak Now.”

Their Relationship

Despite their age difference and differing levels of experience, Taylor and John were infatuated with each other. They were often spotted together at events, their affectionate displays and public declarations of love making headlines around the world.

However, their relationship was far from perfect. Taylor, still in the early stages of her career and life, found that the age gap between the couple was getting too much of an issue. To this day, people speculate about right and wrong, but what happened next shocked everyone…

How it Ended

Their breakup, which came in early 2010, was as tumultuous as their romance. In the aftermath of their split, Taylor famously penned the scathing breakup anthem “Dear John,” in which she lamented the end of their relationship and questioned John’s intentions.

In response to the release of the song and everything that came with it, Mayer said, “It made me feel terrible because I didn’t deserve it. I’m pretty good at taking accountability now and never did anything to deserve that. It was a really lousy thing for her to do.”

Jake Gyllenhaal: The Beginning

Her Age: 20 – 21

Duration of Relationship: October 2010 – January 2011

Similar to her relationship with Mayer, Taylor Swift and Jake Gyllenhaal’s romance was a whirlwind affair that captivated both fans and tabloids alike. Their love story began in the fall of 2010 when they were spotted together at various hotspots in New York City.

Their relationship was marked by outings to coffee shops, walks in Central Park, and cozy dinner dates—typical activities for any couple in the Big Apple. Despite their 10-year age difference, Taylor, then 20, and Jake, 30, seemed to be smitten with each other.

Their Relationship

However, their romance wasn’t without its challenges. Taylor, known for her heartfelt lyrics and emotional vulnerability, reportedly fell hard for Jake. At the same time, he, a notoriously private actor, struggled with the intense scrutiny that came with dating a high-profile musician.

As the paparazzi followed their every move and rumors swirled about their relationship, Taylor and Jake tried to maintain a sense of normalcy. They attended events together, supported each other’s projects, and even spent Thanksgiving with Jake’s family in New York.

How it Ended

After some time, reports surfaced of tension and disagreements, with sources citing their age difference and conflicting schedules as contributing factors to their breakup. In January 2011, just three months after they were first linked together, Taylor and Jake called it quits. The breakup reportedly hit Taylor hard, inspiring several songs on her album “Red,” including the emotional 10-minute ballad “All Too Well.”

After “All Too Well: The Short Film” came out in 2021, Gyllenhaal came out and said, “It has nothing to do with me. It’s about her relationship with her fans,” he said. “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that. At some point, I think it’s important when supporters get unruly that we feel a responsibility to have them be civil and not allow for cyberbullying in one’s name.”

Conor Kennedy: The Beginning

Her Age: 22

Duration of Relationship: July 2012 – October 2012

Taylor Swift and Conor Kennedy’s relationship stirred up quite a buzz when it emerged in the summer of 2012. The unlikely pair, with Taylor being a globally renowned pop star and Conor a member of the prestigious Kennedy family, seemed like a match made in tabloid heaven.

Their romance began amidst the idyllic backdrop of Hyannis Port, Massachusetts, where Taylor was spotted spending time with Conor’s family. Their courtship unfolded in the public eye, with paparazzi capturing their romantic strolls on the beach and cozy dinners with the Kennedys.

Their Relationship

Despite the apparent glamour of their relationship, Taylor and Conor faced challenges that many couples could hardly imagine. Conor, just 18 at the time, was navigating the complexities of adolescence and the weight of his family’s legacy, while Taylor, 22, was grappling with the pressures of fame and the demands of her career.

Their relationship was not without its share of controversies. Taylor’s presence in the Kennedy family circle raised eyebrows, with some questioning whether she was exploiting their legacy for publicity. Meanwhile, rumors of tension between Taylor and Conor’s family members further fueled speculation about the stability of their romance.

How it Ended

In the end, their whirlwind romance proved to be short-lived. By the fall of 2012, Taylor and Conor had called it quits, with conflicting reports emerging about the reasons behind their breakup. Some sources cited distance and conflicting schedules, while others hinted at family disapproval and the strain of their high-profile lifestyles.

Even though their love affair was brief, it will always remind fellow Swifties of the time Taylor almost married into the world of Politics! However, she knows better than anyone when there is such a significant age gap that sometimes things are harder to work out.

Harry Styles: The Beginning

Her Age: 22 – 23

Duration of Relationship: November 2012 – January 2013

Taylor Swift and Harry Styles’ romance sent shockwaves through the entertainment world in 2012. Their love story began in the glitzy world of pop music, where they first crossed paths at an awards show. Sparks flew instantly, and soon, the tabloids were buzzing with rumors of their budding romance.

Their relationship was a whirlwind from the start, marked by lavish vacations, romantic dinners, and public displays of affection. Paparazzi trailed their every move, capturing their intimate moments and fueling speculation about the hottest couple in Hollywood.

How it Ended

In January 2013, just a few months after they were first linked together, Taylor and Harry called it quits. The breakup reportedly hit Taylor hard, inspiring several songs on her album “1989,” including the emotionally charged track “Out of the Woods.”

Since their breakup, the two of them have remained amicable with one another. In 2023, Taylor gave Harry a standing ovation at the Grammy after Styles won the Grammy for Best Pop Vocal Album. After all this time, I think it is safe to say that they are finally “Out of the Woods.”

Calvin Harris: The Beginning

Her Age: 25 – 26

Duration of Relationship: February 2015 – May 2016

Like many of her other relationships, Taylor Swift and Calvin Harris’s relationship sparked excitement among fans and media alike when they first started dating in early 2015. Their romance began quietly, with the two music superstars reportedly meeting through mutual friends.

Their relationship quickly blossomed into a high-profile romance, with Taylor and Calvin frequently spotted together at events and sharing glimpses of their love on social media. They seemed like the perfect match—a powerhouse couple with talent, charisma, and a shared passion for music.

Their Relationship

As their romance flourished, Taylor and Calvin’s relationship became the envy of many. They enjoyed romantic getaways and lavish date nights and even collaborated on music together, with Calvin producing Taylor’s hit song “This Is What You Came For.”

However, despite their picture-perfect image, Taylor and Calvin’s relationship faced its fair share of challenges. The pressures of fame, busy schedules, and constant media scrutiny took a toll on their romance. Like many things in life, nothing lasts forever…

Tom Hiddleston: The Beginning

Her Age: 26

Duration of Relationship: May 2016 – September 2016

This is around the time in Taylor’s dating history when we see a turn towards British men… Taylor Swift and Tom Hiddleston’s whirlwind romance took the world by storm in the summer of 2016. Their love story began shortly after Taylor’s breakup with Calvin Harris when photos surfaced of the two dancing together at a star-studded event…

Their relationship seemed to escalate at lightning speed, so quick that many people speculated about infidelity on Taylor’s part when dating Harris. Paparazzi trailed their every move, capturing their affectionate displays and fueling speculation about the hottest couple in Hollywood.

Their Relationship

Despite their seemingly idyllic romance, Taylor and Tom faced skepticism and scrutiny from the media and fans alike. Some questioned the authenticity of their relationship, suggesting it was a publicity stunt or rebound fling.

As their romance played out in the public eye, rumors of tension and drama behind the scenes began to surface. Many people began to speculate that this whole relationship was, in one way or another, a short fling, seeing as Taylor had very quickly started dating Hiddleston after her breakup with Calvin Harris.

How it Ended

In September 2016, just three months after they were first photographed together, Taylor and Tom called it quits. Their breakup reportedly came as a shock to many, with sources citing the pressures of fame and the intensity of their whirlwind romance as contributing factors.

In the aftermath of their split, Taylor and Tom went their separate ways, with both parties maintaining a relatively low profile in the months that followed. Their brief but intense relationship was no doubt full of excitement and love. But in the end, it just wasn’t enough for either of them…

Joe Alwyn: The Beginning

Her Age: 27 – 33

Duration of Relationship: May 2017 – April 2023

There is no denying that this next relationship was probably one of the most influential in her entire life. Seeing as they were together for more than 6 years, it only makes sense that this was a life-altering relationship. And so continues Taylor’s obsession with British men!

Their relationship was a departure from Taylor’s previous high-profile romances, marked by a sense of privacy and discretion. Unlike her previous relationships, Taylor and Joe kept their love out of the public eye, choosing instead to nurture their bond away from the scrutiny of the media.

Their Relationship

Unlike Taylor’s other relationships, Joe was there during many album releases, meaning that in recent years, a lot of her music has been heavily influenced by him. The pair managed to keep a lot of their relationship private, which was rather important to both Taylor and Joe.

However, even after what seemed like a long, beautiful, and prosperous relationship, the pair announced their shocking split in 2023. But in true Taylor style, she left many cryptic messages for her fans to understand that the pair had called it quits.

How it Ended

Their relationship faced its fair share of challenges, including long distance and the pressures of fame, which eventually took a serious toll on their relationship. Swift had already begun her Eras Tour around the world when the news broke out about the pair.

It was fair to say that fans everywhere were shocked by the news, seeing as how much Joe was a part of her life. But obviously, the pair knew something wasn’t right and decided to end things. Many speculate that Joe couldn’t handle the amount of attention Taylor was getting… It’s a shame he couldn’t see how lucky he was.

Matty Healy: The Beginning

Her Age: 33

Duration of Relationship: May 2023 – June 2023

There are some relationships that, even though they were important for some reason or another, might not have been the best life decision. We are all guilty of having been in somewhat of a rebound relationship like this… And for Taylor Swift, this person was the lead singer of none other than The 1975, Matty Healy.

Another British love interest, this romance was short-lived… At first glance, this pairing seems completely wrong, considering their different musical backgrounds and their general demeanor. However, that didn’t stop the pair from sharing a short dating stint in 2023.

Their Relationship

At the time, many people were confused about this particular pairing, but seeing as Miss Swift had just gone through a breakup, people seemed to understand this romance in a specific way. And having been friends since 2014, the two musicians had already crossed paths many years before.

For the most part, Matty Healy is seen as a rowdy, intellectually stimulated British rock star who probably never would have stood a chance with Swift if it hadn’t happened at this exact moment in time. However, everyone gets to make a few mistakes when it comes to love, right?

How it Ended

When the pair called it quits after roughly a month or so of dating, fans weren’t very shocked. However, it did seem like Healy potentially took the breakup a little bit harder than Swift. Seeing as she was in the middle of her world tour, she probably had bigger things to think about…

Matty Healy even showed up to one of her concerts in Nashville at the beginning of the Eras Tour, which showed her fans that perhaps he was committed. But as we previously stated, the pair were far from suited, but we’re sure the two have remained friends.

Travis Kelce: The Beginning

Her Age: 33 – Today

Duration of Relationship: June 2023 – Today

There is no denying that Taylor Swift has had her fair share of dating issues throughout her many years in the spotlight. So when there finally comes a time where it seems as though she has found “the one,” there is nothing left to do but just feel joy.

It’s almost as if she prophesized this love affair with one of her lyrics from her song “Fifteen,” “Dating the guy on the football team.” Taylor Swift and Kansas City Chiefs Tight End started dating in 2023, and it is safe to say that it seems like these two are going strong.

Their Relationship

In a December 2023 interview, Taylor let us in on how they started dating, “We started hanging out right after that. So we actually had a significant amount of time that no one knew, which I’m grateful for because we got to get to know each other. By the time I went to that first game, we were a couple. I think some people think that they saw our first date at that game. We would never be psychotic enough to hard launch a first date.”

Continuing, she said, “When you say a relationship is public, that means I’m going to see him do what he loves, we’re showing up for each other, other people are there, and we don’t care. The opposite of that is you have to go to an extreme amount of effort to make sure no one knows that you’re seeing someone. And we’re just proud of each other.”

Where Will Things Go?

Like anything in life, there is no telling where this relationship might lead, but we can only hope that Taylor has finally found her prince charming in Chiefs Tight End Travis Kelce. The pair continue to show up for one another, both in private and public, which is undoubtedly the most important thing in a relationship.

The one thing that separates this pairing to the many others is that Taylor is finally in place where she knows who she is, what she wants and where her life is heading. For now, all we Swifties can do is hope that this adorable relationship lasts between these two!