Taylor Swift's Exes: A Timeline Of Her Relationships

Oct 30, 2025 by Team 53 views

Hey Swifties! Let's dive into the whirlwind world of Taylor Swift's past relationships. Over the years, Taylor has dated some seriously high-profile guys, and each relationship has, of course, given us iconic songs! So, grab your calendars, and let's take a trip down memory lane, listing Taylor Swift's boyfriends in order, complete with ages and a little bit about each romance. Let's get started!

A Deep Dive into Taylor's Romantic History

Before we jump into the specifics, it's important to remember that relationships are complex, and what we see in the media is just a small fraction of the real story. Taylor Swift has always poured her heart into her music, and her relationships have often served as inspiration. Each relationship, whether short-lived or more extended, has marked a specific era in Taylor's life and career, and it's through these experiences that she has evolved as an artist and as a person. Also, everyone deserves privacy and respect, and focusing on the positive aspects of how these experiences shaped her music is key. It's fascinating to see how Taylor's songwriting reflects her personal growth and changing perspectives on love. From the fairytale innocence of her early albums to the more nuanced and mature themes in her later work, her discography is a testament to her journey through love and life. We, as fans, have the privilege of witnessing this evolution through her art, and it's a connection that makes her music so relatable and enduring. Each chapter in her romantic history has not only provided fodder for countless headlines but has also contributed to the rich tapestry of her musical narrative. It is so exciting to analyze how each relationship has influenced her songwriting and shaped the different eras of her career.

Taylor Swift's Boyfriends List in Order with Ages

Alright, here is the list you've all been waiting for. We’re breaking down Taylor Swift's romantic connections in chronological order. Here we go:

1. Brandon Borello (2006)

Age When Dating Taylor: Unknown
A Quick Look: Taylor's high school sweetheart. Not much is publicly known about Brandon, but he marks the beginning of Taylor's very public dating life. Every superstar has to start somewhere, and Brandon Borello holds a special place in the early chapters of Taylor Swift's romantic history. While details about their relationship are scarce, it's clear that this early romance played a significant role in shaping Taylor's initial perspectives on love and relationships. High school sweethearts often share a unique bond, experiencing many firsts together and laying the foundation for future romantic endeavors. Although their time together may have been brief, the impact of Brandon Borello on Taylor Swift's life should not be underestimated. As her first public relationship, it provided valuable lessons and experiences that likely influenced her approach to love and songwriting in the years that followed. It's fascinating to consider how this early romance might have shaped the themes and emotions explored in her early music, setting the stage for the heartfelt and relatable lyrics that would eventually resonate with millions of fans around the world. While the specifics of their relationship remain largely private, the significance of Brandon Borello in Taylor Swift's personal and artistic development cannot be denied. He represents the beginning of a journey that would see her navigate the complexities of love and relationships under the intense scrutiny of the public eye.

2. Sam Armstrong (2006)

Age When Dating Taylor: Unknown
A Quick Look: Another early relationship. Sam reportedly inspired Taylor's song "Should've Said No." We all know how Taylor turns heartbreak into bops! Sam Armstrong's brief but impactful relationship with Taylor Swift has become the stuff of legend, largely thanks to the scathing lyrics of "Should've Said No." The song, a raw and emotional account of infidelity, catapulted Taylor into the spotlight and established her as a fearless songwriter unafraid to tackle personal experiences in her music. While the details of their relationship remain shrouded in mystery, the impact of Sam's alleged betrayal is undeniable. It not only fueled one of Taylor's early hits but also set a precedent for her future songwriting, which would often draw inspiration from her romantic relationships. "Should've Said No" resonated deeply with fans who had experienced similar heartbreak, cementing Taylor's status as a relatable and authentic voice for young women everywhere. The song's success also highlighted Taylor's ability to turn personal pain into universal anthems, a skill that would serve her well throughout her career. Sam Armstrong's legacy, whether he likes it or not, is forever intertwined with Taylor Swift's rise to fame. He represents a pivotal moment in her artistic development, a catalyst for the creation of a song that would define her early sound and establish her as a force to be reckoned with in the music industry.

3. Joe Jonas (2008)

Joe's Age When Dating Taylor: 18-19
A Quick Look: A short but very public relationship with one of the Jonas Brothers. Their breakup was rumored to be via a very brief phone call. Ouch! Joe Jonas and Taylor Swift's whirlwind romance in 2008 was a pop culture phenomenon, captivating fans and dominating headlines. As two of the biggest teen stars at the time, their relationship was a match made in pop heaven, complete with red carpet appearances and adoring fans. However, their romance was short-lived, ending abruptly with a rumored 27-second phone call that became infamous in the tabloids. Despite the brevity of their relationship, the impact of Joe Jonas on Taylor Swift's life and music is undeniable. He is widely believed to be the inspiration behind several of her songs, including "Forever & Always" and "Last Kiss," which offer contrasting perspectives on their breakup. "Forever & Always" captures the shock and disbelief of a sudden end to a relationship, while "Last Kiss" reflects on the bittersweet memories of their time together. Joe Jonas represents a significant chapter in Taylor Swift's romantic history, a period of intense media scrutiny and public fascination. Their relationship not only provided fodder for her songwriting but also shaped her understanding of love and relationships in the spotlight. While their romance may have ended abruptly, the memories and experiences they shared continue to resonate in her music and remain a topic of conversation among fans.

4. Lucas Till (2009)

Lucas' Age When Dating Taylor: 18-19
A Quick Look: This was a brief romance that occurred after Lucas appeared in Taylor's "You Belong With Me" music video. It didn't last long, as they reportedly were better as friends. Lucas Till and Taylor Swift's brief but memorable romance blossomed after Lucas starred in Taylor's iconic "You Belong With Me" music video. The video, a quintessential tale of unrequited love, catapulted both Taylor and Lucas to new heights of fame and sparked a real-life connection between the two young stars. While their relationship was short-lived, it captured the hearts of fans who had rooted for them in the video. Lucas Till represents a chapter in Taylor Swift's life where art imitated reality, and the lines between fantasy and real-life romance blurred. Their connection, though brief, highlighted the power of music and visuals to create compelling narratives and spark genuine connections. Lucas' appearance in the "You Belong With Me" video solidified his place in Taylor Swift lore, and their subsequent relationship, however fleeting, added another layer of intrigue to their story. While they ultimately decided they were better off as friends, their time together remains a cherished memory for fans and a reminder of the magic that can happen when music and love intertwine.

5. Taylor Lautner (2009)

Taylor's Age When Dating Taylor: 17
A Quick Look: Taylor Squared! This was a fan-favorite pairing. He is rumored to be the inspiration behind "Back to December." Taylor Lautner and Taylor Swift's relationship, affectionately dubbed "Taylor Squared" by fans, was a media frenzy from the start. As two of the biggest young stars in Hollywood, their romance captured the hearts of millions and sparked a wave of excitement that few celebrity couples can match. Taylor Lautner, known for his role in the Twilight saga, and Taylor Swift, the reigning queen of country-pop, seemed like the perfect match, and their every move was followed by paparazzi and adoring fans. While their relationship was relatively short-lived, its impact on pop culture is undeniable. Taylor Lautner is widely believed to be the inspiration behind Taylor Swift's heartfelt ballad "Back to December," a song of regret and remorse that offers a glimpse into the complexities of their breakup. The song resonated deeply with fans who had invested in their relationship, and it remains a fan favorite to this day. Taylor Lautner represents a chapter in Taylor Swift's life where young love collided with the pressures of fame, creating a whirlwind of media attention and public scrutiny. Despite the challenges they faced, their relationship remains a cherished memory for fans and a reminder of the magic that can happen when two stars align.

6. John Mayer (2009-2010)

John's Age When Dating Taylor: 32-33
A Quick Look: This relationship was controversial due to the age gap. Taylor reportedly wrote "Dear John" about him, which is quite a scathing song. John Mayer and Taylor Swift's relationship remains one of the most talked-about romances in Taylor Swift's history, largely due to the significant age gap between the two musicians. The relationship, which occurred when Taylor was just 19 and John was 32, sparked controversy and raised questions about the power dynamics at play. Despite the criticism, their romance played out in the public eye, with paparazzi capturing their every move and fueling speculation about their dynamic. John Mayer is widely believed to be the inspiration behind Taylor Swift's scathing ballad "Dear John," a song that lays bare the pain and confusion of a young woman navigating a relationship with an older, more experienced man. The song is a raw and emotional account of manipulation and emotional abuse, and it remains one of Taylor Swift's most powerful and controversial tracks. John Mayer represents a chapter in Taylor Swift's life where she grappled with the complexities of love and power, learning valuable lessons about self-worth and the importance of healthy relationships. Their romance, though controversial, ultimately served as a catalyst for her growth as an artist and as a person.

7. Jake Gyllenhaal (2010)

Jake's Age When Dating Taylor: 29-30
A Quick Look: Another very public and talked-about relationship. Many believe "All Too Well" is about him, and the All Too Well 10-minute version just added fuel to the fire! Jake Gyllenhaal and Taylor Swift's relationship was a whirlwind romance that captivated fans and dominated headlines in the fall of 2010. As two of the biggest stars in Hollywood, their pairing was a media frenzy from the start, with paparazzi following their every move and fans eagerly anticipating their next public appearance. Despite the intense scrutiny, Jake and Taylor seemed genuinely happy, and their romance quickly became the talk of the town. However, their relationship was short-lived, ending abruptly after just a few months. The breakup left fans heartbroken and sparked a wave of speculation about the reasons behind their split. Jake Gyllenhaal is widely believed to be the inspiration behind Taylor Swift's iconic song "All Too Well," a heart-wrenching ballad that captures the pain and longing of a lost love. The song is a masterpiece of storytelling, painting a vivid picture of their relationship and its tragic end. "All Too Well" has become a fan favorite and is widely considered one of Taylor Swift's best songs. The recent release of the 10-minute version of "All Too Well" only added fuel to the fire, confirming fans' suspicions and sparking a renewed interest in their relationship. Jake Gyllenhaal represents a chapter in Taylor Swift's life where she experienced the highs and lows of love under the intense scrutiny of the public eye. Their romance, though brief, left an indelible mark on her life and music, and it continues to fascinate fans to this day.

8. Conor Kennedy (2012)

Conor's Age When Dating Taylor: 18
A Quick Look: This was a summer romance with a Kennedy! It was short and sweet, but definitely a notable chapter in Taylor's dating history. Conor Kennedy and Taylor Swift's summer romance in 2012 was a surprising and intriguing chapter in Taylor's dating history. As a member of the prestigious Kennedy family, Conor brought a new level of fame and intrigue to Taylor's already high-profile love life. Their relationship, which blossomed in the summer of 2012, was closely followed by the media and fans alike, with paparazzi capturing their every move. Despite the intense scrutiny, Conor and Taylor seemed to enjoy their time together, spending their days sailing, strolling along the beach, and enjoying the idyllic atmosphere of the Kennedy compound in Hyannis Port. However, their romance was short-lived, ending after just a few months. The reasons behind their split remain a mystery, but it's clear that the pressures of fame and the challenges of maintaining a relationship in the public eye played a role. Conor Kennedy represents a chapter in Taylor Swift's life where she stepped into a new world of privilege and political influence. Their romance, though brief, offered a glimpse into a different side of Taylor's personality and expanded her horizons in unexpected ways. While their relationship may have ended, the memories and experiences they shared remain a unique and memorable part of Taylor Swift's romantic history.

9. Harry Styles (2012-2013)

Harry's Age When Dating Taylor: 18-19
A Quick Look: Haylor! This was a huge pop culture moment. They were spotted everywhere, and their breakup was just as public. Many believe "Style" and other 1989 tracks are about Harry. Harry Styles and Taylor Swift's relationship, affectionately dubbed "Haylor" by fans, was a pop culture phenomenon that dominated headlines and social media feeds in late 2012 and early 2013. As two of the biggest stars in the world, their pairing was a match made in teen idol heaven, and their every move was followed by paparazzi and adoring fans. Harry, the heartthrob from One Direction, and Taylor, the reigning queen of pop, seemed like the perfect couple, and their romance quickly became the talk of the town. However, their relationship was short-lived, ending abruptly after just a few months. The breakup left fans heartbroken and sparked a wave of speculation about the reasons behind their split. Harry Styles is widely believed to be the inspiration behind several of Taylor Swift's songs, including "Style," "Out of the Woods," and "Perfectly Good Heart." These songs offer a glimpse into the complexities of their relationship and the challenges they faced as a couple in the public eye. Harry Styles represents a chapter in Taylor Swift's life where she experienced the highs and lows of love under the intense scrutiny of the media. Their romance, though brief, left an indelible mark on her life and music, and it continues to fascinate fans to this day.

10. Calvin Harris (2015-2016)

Calvin's Age When Dating Taylor: 31-32
A Quick Look: This was a longer relationship for Taylor, and it seemed pretty serious. They even collaborated on music! The breakup was rumored to be messy. Calvin Harris and Taylor Swift's relationship was one of Taylor's longest and most public romances to date. The couple, who began dating in early 2015, quickly became one of the most talked-about pairs in the entertainment industry, gracing red carpets, attending awards shows, and sharing romantic photos on social media. Calvin, a successful DJ and producer, and Taylor, the reigning queen of pop, seemed like the perfect match, and their relationship quickly became the envy of fans around the world. However, their romance was not without its challenges. The couple faced intense scrutiny from the media and struggled to maintain their privacy in the face of constant public attention. Despite these challenges, Calvin and Taylor remained committed to each other, and their relationship seemed to be going strong. However, in early 2016, rumors began to swirl that the couple was on the rocks. These rumors were confirmed when Calvin and Taylor announced their breakup in June of that year. The breakup was reportedly messy, with both sides airing their grievances in the media. Calvin Harris represents a chapter in Taylor Swift's life where she experienced the challenges of maintaining a long-term relationship in the public eye. Their romance, though ultimately unsuccessful, taught her valuable lessons about love, commitment, and the importance of privacy.

11. Tom Hiddleston (2016)

Tom's Age When Dating Taylor: 35
A Quick Look: Hiddleswift! This was a whirlwind romance that was very public and very short. Remember the "I Heart T.S." shirt? Tom Hiddleston and Taylor Swift's relationship, dubbed "Hiddleswift" by the media, was a whirlwind romance that captivated the world in the summer of 2016. The couple, who began dating just weeks after Taylor's breakup with Calvin Harris, embarked on a whirlwind tour of the world, visiting exotic locations, attending red carpet events, and sharing romantic photos on social media. Tom, a successful actor known for his role as Loki in the Marvel Cinematic Universe, and Taylor, the reigning queen of pop, seemed like an unlikely match, but their romance quickly became the talk of the town. However, their relationship was not without its critics. Many questioned the authenticity of their romance, suggesting that it was a publicity stunt designed to boost their careers. Despite these criticisms, Tom and Taylor seemed genuinely happy, and their romance continued to blossom. However, their relationship was short-lived, ending after just a few months. The reasons behind their split remain a mystery, but it's clear that the pressures of fame and the challenges of maintaining a relationship in the public eye played a role. Tom Hiddleston represents a chapter in Taylor Swift's life where she experienced the highs and lows of a whirlwind romance. Their relationship, though brief, left an indelible mark on her life and career, and it continues to fascinate fans to this day.

12. Joe Alwyn (2016-2023)

Joe's Age When Dating Taylor: 25-32
A Quick Look: This was Taylor's longest relationship. It was very private, and many thought they were endgame. Alas, it wasn't meant to be. Joe Alwyn and Taylor Swift's relationship was a study in contrasts, a stark departure from Taylor's previous high-profile romances. The couple, who began dating in late 2016, made a conscious effort to keep their relationship out of the public eye, shunning red carpets, avoiding paparazzi, and rarely speaking about each other in interviews. Joe, a talented actor known for his roles in films like "The Favourite" and "Billy Lynn's Long Halftime Walk," and Taylor, the reigning queen of pop, seemed to value their privacy and were determined to protect their relationship from the prying eyes of the media. For several years, their strategy seemed to work. Joe and Taylor maintained a low profile, enjoying quiet dates, spending time with family and friends, and supporting each other's careers. Many believed that they were endgame, that Taylor had finally found her forever partner. However, in early 2023, rumors began to swirl that the couple was on the rocks. These rumors were confirmed when Taylor and Joe announced their breakup in April of that year. The breakup left fans heartbroken and sparked a wave of speculation about the reasons behind their split. Joe Alwyn represents a chapter in Taylor Swift's life where she prioritized privacy and sought a more grounded and stable relationship. Their romance, though ultimately unsuccessful, taught her valuable lessons about love, commitment, and the importance of maintaining a sense of normalcy in the face of fame.

13. Matty Healy (2023)

Matty's Age When Dating Taylor: 34
A Quick Look: This was a short-lived and controversial relationship that occurred shortly after her breakup with Joe Alwyn. Matty Healy and Taylor Swift's relationship was a brief but highly controversial chapter in Taylor's dating history. The couple, who were rumored to have dated briefly in the past, reconnected in early 2023, just weeks after Taylor's breakup with Joe Alwyn. Their romance sparked a firestorm of criticism, with many fans questioning Taylor's choice of partner. Matty, the frontman of the band The 1975, has a reputation for making controversial and offensive statements. Despite the criticism, Taylor and Matty seemed determined to make their relationship work. They were spotted together on several occasions, attending concerts, holding hands, and sharing romantic moments. However, their romance was short-lived, ending after just a few weeks. The reasons behind their split remain a mystery, but it's clear that the intense public scrutiny and the controversy surrounding Matty's past played a role. Matty Healy represents a chapter in Taylor Swift's life where she faced intense public criticism for her choice of partner. Their romance, though brief, taught her valuable lessons about the importance of choosing partners who align with her values and the need to be mindful of the impact of her relationships on her fans.

14. Travis Kelce (2023-Present)

Travis' Age When Dating Taylor: 34
A Quick Look: This relationship is ongoing as of late 2023 and has taken the world by storm! A football star and a pop star – it's a match made in pop culture heaven! Travis Kelce and Taylor Swift's relationship has quickly become one of the most talked-about romances of 2023. The couple, who were first linked in September of that year, have captivated the world with their whirlwind romance, gracing headlines, trending on social media, and sparking a frenzy of excitement among fans. Travis, a star tight end for the Kansas City Chiefs, and Taylor, the reigning queen of pop, seemed like an unlikely match, but their connection has proven to be undeniable. They have been spotted together at football games, on dates in New York City, and even on a romantic getaway to Argentina. Their relationship has not only captured the hearts of fans but has also brought unprecedented attention to the NFL. Taylor's appearances at Chiefs games have led to a surge in viewership, and Travis has become a household name. Travis Kelce represents a new chapter in Taylor Swift's life, one where she is embracing love and happiness with a partner who is equally successful and confident. Their romance is a celebration of two worlds colliding, a testament to the power of love to transcend boundaries and bring people together.

Final Thoughts

Wow, what a journey through Taylor Swift's romantic history! From high school sweethearts to Hollywood heartthrobs, Taylor has certainly had an interesting dating life, which has, of course, provided incredible inspiration for her music! Each relationship has marked a specific era in her life and career, and it's through these experiences that she has evolved as an artist and as a person. Who knows what the future holds for Taylor and her love life? One thing is for sure: we'll be here to listen to the songs that come out of it! Keep shining, Taylor!