echo Got a long list of ex-lovers? That was what defined Taylor Swift for the longest time. Taylor’s dating history has been as compelling as her music itself. However, regardless of the public’s opinion, she embraced it in her work, making it into a source of creative power. Turning a series of heartbreaks and experiences into what we have now – a paradigm-shifting music industry.
No doubt, Taylor’s discography is deeply intertwined with her personal life; each chapter of her life is documented within her songs as she journeys on with experiencing love, heartbreak, and everything in between. With her relationships as a key inspiration for many of her all-time favourites like ‘Back to December’, ‘Dear John’, ‘All Too Well’ and the list goes on, it portrays the powerful impact of channeling one’s experiences into a driving force behind a career built entirely on honest storytelling. We will explore Taylor Swift’s full-circle journey, diving into her past relationships and how they have significantly influenced her songwriting and defined the different eras of her career.
- Joe Jonas
Taylor Swift’s very first public romance was with Joe Jonas, way back in 2008. At the time, Taylor was only 18, and while the relationship only lasted a few months, it made an undoubtedly large impact on both fans, the media and Taylor’s discography. When guest starring on The Ellen DeGeneres Show, Taylor revealed that the Jonas brother broke things off over a 27-second phone call (yikes!).
This breakup led to the birth of some iconic Taylor hits during the Fearless era, including ‘Forever & Always’, ‘Mr. Perfectly Fine’, ‘Better Than Revenge’ and ‘You All Over Me’. Looking back, the Joe era feels almost innocent; a high school crush gone wrong, complete with public drama and heartbreak anthems that fueled her early career.
“Goodbye Mr. “Casually cruel”
Mr. “Everything revolves around you”
I’ve been Miss “Misery” for the last time
And you’re Mr. “Perfectly Fine“”
~ ‘Mr. Perfectly Fine’ by Taylor Swift ~
- Lucas Till
Remember when Taylor Swift made a cameo in Hannah Montana: The Movie back in 2009? That’s where she first crossed paths with Lucas Till. Not long after, he popped up as the lead in her now-iconic ‘You Belong With Me’ music video.
Unlike some of Taylor’s previous romance, her fling with Till was refreshingly low-drama. Their relationship was so short, that no official or strongly suspected Taylor songs are about Lucas Till. He’s one of the rare exes who escaped the Swiftian lyrical canon unharmed.
Lucas Till and Taylor Swift in the ‘You Belong With Me’ music video
- Taylor Lautner
Ah, Taylor Lautner; a personal favourite of mine (writer is proudly team Jacob wink). Taylor Lautner and Taylor Swift first met on the set of the 2010 film Valentine’s Day. While ‘Taylor Squared’ had a short and brief run, it was sweet and one of the healthiest chapters in Taylor’s dating history. Lautner was reportedly nothing short of caring and affectionate, to which unfortunately, Swift didn’t reciprocate as strongly, leading to the end of their chapter.
Taylor Swift and Taylor Lautner stepping out for dinner back in 2009
However, this relationship led to Taylor’s infamous apology song, ‘Back To December’, where she highlighted her regret for letting go of a healthy and drama-free relationship. What makes the Taylor Squared era so unique is it gives fans a glimpse of a more vulnerable side to Swift; she owns up to her mistakes and acknowledges the guilt of not providing the love men like Lautner are so deserving of.
“I miss your tan skin, your sweet smile
So good to me, so right
And how you held me in your arms that September night
The first time you ever saw me cry”
~ ‘Back To December’ by Taylor Swift ~
Taylor Swift and Taylor Lautner attending a hockey game in October 2009
Today, Taylor considers Lautner one of her best friends. Lautner starred in Taylor’s ‘I Can See You’ music video, and made a few surprise appearances on stage of her Eras Tour shows. Ironically, Lautner tied the knot with yet another Taylor, Taylor Dome, who just so happens to be a Swiftie herself!
“But if we loved again, I swear I’d love you right
I’d go back in time and change it, but I can’t
So if the chain is on your door, I understand”
~ ‘Back To December’ by Taylor Swift ~
- John Mayer
A massive fan turned partner of John Mayer for about 3 months. It all began with a Tweet by John, stating that he was interested to record with her. John’s ‘Half of My Heart’ song marked the pair’s first (and last) collaboration. Their first performance together at the Z100 Jingle Ball hit the news. What drew the attention towards their relationship was their 13 years age gap, when Taylor was 19 then. Not to mention, the release of ‘Dear John’ stunned the public as it displays Taylor’s portrayal of being manipulated by an older man. John’s response to said song fanned the flames as he critiqued that “it’s kind of cheap songwriting” and “lousy thing for her to do” in a 2012 interview with Rolling Stone. The bad blood for him continues on even till recent years. From receiving backlash from Taylor’s fans in an attempted TikTok video to even receiving death threats upon the release of her re-recording of her album ‘Red’.
While this relationship took place a long time ago, some people are still upset about it. Taylor, however, is not. Before performing ‘Dear John’ on The Eras Tour, she clarified that the song was now a piece of art she’s simply proud of. She’s also asked fans to practice kindness and gentleness, and to not speculate about who the song might be about. It is safe to say that this chapter of her life is now in the past and Taylor has moved on.
Dear John, I see it all now, it was wrong
Don’t you think nineteen’s too young
To be played by your dark, twisted games when I loved you so?
I should’ve known
~ ‘Dear John’ by Taylor Swift ~
John Mayer and Taylor Swift performs duet ‘Half of My Heart’
- Jake Gyllenhaal
The Jake era. Painfully heartbreaking, but somehow, it’s the chapter us fans simply can’t stop looking back on. Jake Gyllenhaal, in relation to Taylor Swift, is, if anything, a symbol. He’s the red scarf. He’s the birthday party he skipped. He’s the autumn leaves. And most importantly, he’s the gnawing feeling of being too young for someone who should’ve known better for their age.
Jake Gyllenhaal and Taylor Swift
The most obvious thing to define Jake Gyllenhaal and Taylor Swift’s relationship is the 9-year age gap, with Taylor being just 20 at the time, while Jake was 29. The Jake era showed us Taylor’s transition from a heartbroken teenager craving love from someone she’d hoped was mature enough to give it, to a woman spending her first adult year completely devastated.
The couple were spotted by paparazzi walking hand-in-hand through Brooklyn in the autumn of 2010, and she later spent Thanksgiving with his family. However, in ‘The Moment I Knew’, Taylor sings of Jake’s absence from her 21st birthday, which further led to the release of ‘We Are Never Ever Getting Back Together’, ‘All Too Well’, and its many variations, including a detailed 10-minute version and the infamous short film.
“And there we are again when nobody had to know
You kept me like a secret, but I kept you like an oath
Sacred prayer and we’d swear
To remember it all too well”
~ ‘All Too Well’ by Taylor Swift ~
Dylan O’Brien and Sadie Sink in ‘All Too Well: The Short Film’
While we can never justify heartbreak and toxicity in relationships, there’s absolutely no denying that Taylor’s relationship with Jake shaped her ‘Red’ album and kickstarted a new era as both a songwriter and entertainer. Songs like ‘All Too Well’ perfectly showcase Taylor’s emotional writing and her use of symbolism.
“And you call me up again just to break me like a promise
So casually cruel in the name of being honest
I’m a crumpled up piece of paper lying here
‘Cause I remember it all, all, all”
~ ‘All Too Well’ by Taylor Swift ~
- Conor Kennedy
Then came the short-lived romance with Conor Kennedy that lasted only 3 months. The 22-year-old and her 18-year-old beau were first photographed together in Massachusetts during the summer of 2012.
Dating back to when they first crossed paths, Conor’s aunt, Rory Kennedy, invited Taylor to screenings for her documentary on her mother, Ethel Kennedy. The singer gradually bonded with the Kennedy family, providing emotional comfort and support to them following the passing of Mary Richardson Kennedy, Conor’s mother, a few months prior.
Taylor Swift visiting Mary Kennedy’s grave with the Kennedy’s
Curious minds sparked when news caught wind that she bought a home not far from the Kennedy’s in Hyannis Port, Massachusetts. Many viewed this as a controversial move considering that they were in the early stages of the relationship, and the age gap such that Conor was still in high school. Nonetheless, it was indefinitely an investment. Vanity Fair reported that the property was resold for $1 million after her summer fling with Conor ended that September.
Taylor’s ‘Begin Again’ in the ‘Speak Now’ album was believed to be about the beginning of her relationship with Conor, describing the feelings of finding a new spark after heartbreak upon her breakup with Jake. Additionally, the Kennedy family’s history, specifically the courtship of Conor’s grandparents, Ethel Kennedy and Robert F. Kennedy has inspired the dreamy song of “Starlight”. A black-and-white picture of them dancing turned into an imagination of the ideal teenage romance everyone longs for.
I’ve been spending the last eight months
Thinking all love ever does
Is break and burn, and end
But on a Wednesday in a cafe
I watched it begin again
~ ‘Begin Again’ by Taylor Swift ~
- Harry Styles
One of Taylor’s most impactful relationships for both media and her music was with Harry Styles – or should I say, “Style” (underrated pop song in my humble opinion). For Harry, one-fifth of the global sensation One Direction, the romance lasted for 3 months in late 2012. Similar to the age gap with Conor, at that time, Harry was 18 and Taylor was 22. Throughout the course of their relationship, their time together was marked by intense paparazzi attention and drama, with their meet-ups constantly making headlines.
Taylor Swift and Harry Styles spotted in Central Park
Their relationship was brief but turbulent. Regardless, their union sparked a massive fan crossover between the Directioners and Swifties, ultimately influencing the music industry in some ways. From subtle hints of Taylor wearing Harry’s silver airplane necklace in ‘Out Of The Woods’ to referencing events during their relationship in ‘Is It Over Now?’ Things took a toll when Taylor was spotted leaving the island alone during their vacation, while Harry stayed behind and paid a visit to Richard Branson’s private island. Rumours had it that she confronted him for being with another girl. Soon, sources confirmed that they had indeed split following their Caribbean getaway.
When you lost control (uh-huh)
Red blood, white snow (uh-huh)
Blue dress on a boat (uh-huh)
Your new girl is my clone
~ ‘Is It Over Now?’ by Taylor Swift ~
Over the years, both showed that they had moved on, especially when they reunited at the 2014 Victoria’s Secret Fashion Show afterparty a year later and the 2021 Grammy Awards.
Taylor Swift and Harry Styles at the 2021 Grammy Awards
- Calvin Harris
A 15-month long relationship with Scottish DJ Calvin Harris began in early 2015, making it her longest relationship to date at the time. They first met at the Elle Style Awards in February and went public a few months later at the 2015 Billboard Music Awards. During their time together, they collaborated on ‘This is What You Came For’ which featured Rihanna. In June 2016, Calvin broke things off. Following the split, it was revealed that Taylor had co-written the song under the pseudonym Nils Sjöberg.
Interestingly, Calvin did not make Taylor Swift’s typical breakup songwriting cycle. There were almost no songs that are primarily about him. Most were more about the circumstances of the relationship ending and the immediate transition to her next romance, simply like her lyrics in ‘Getaway Car’. Conversely, Calvin did address their situation through his track ‘Olé’ that was interpreted as accusing Taylor of cheating on him, referencing the quick jump to her next relationship.
Taylor Swift and Calvin Harris
- Tom Hiddleston
In 2016, merely a few weeks following her split with Calvin Harris, Taylor found herself in a fling with actor Tom Hiddleston, though this relationship was anything but loki (get it?). The two were seen kissing on the beach, dancing at the Met Gala and a Selena Gomez concert, and Tom was even seen wearing a ‘I HEART TS’ tank top!
Tom Hiddleston and Taylor Swift
The pair called it quits only a few months later, which inspired ‘Getaway Car’ from Taylor’s ‘Reputation’ album. The song paints their relationship as fast-paced, flashy and as an escape, rather than anything genuine, suggesting Tom was simply a rebound (fitting for the God of Mischief, I guess).
“You were drivin’ the getaway car
We were flyin’, but we’d never get far
Don’t pretend it’s such a mystery
Think about the place where you first met me”
~ ‘Getaway Car’ by Taylor Swift ~
- Joe Alwyn
The relationship with British actor Joe Alwyn marked Taylor’s longest and most secretive romance, lasting six years from late 2016 to April 2023. Joe Alwyn – or should I say, William Bowery – was a figure who significantly played a role in both Taylor’s personal life and songwriting. Their first encounter at the 2016 Met Gala grew to become a love story Taylor thought she would never experience.
In contrast to her previous high-profile relationships, this one was defined by its intensity on privacy and trust. In Taylor’s documentary, Miss Americana, she spoke of “falling in love with someone who had a wonderfully normal, balanced life.” Joe Alwyn was a perfect match as he himself was a humble, down-to-earth person. Not to mention, despite Taylor’s bad rep that peaked during the Reputation era, he remained by her side through it all, loving her despite her flaws.
Taylor Swift and Joe Alwyn in New York City
Their connection went beyond just morally supporting each other’s careers but embarking on an adventure in exploring artistic collaboration. Hence, the birth of the pseudonym William Bowery (a name combining the name of Joe’s grandfather, William, and the street of a New York art gallery).
Joe’s influence can be noted across the albums folklore, evermore, and Midnights where he played a significant role as a co-writer and co-producer on several songs. This includes masterpieces such as ‘exile’, ‘betty’, ‘champagne problems’, ‘Sweet Nothing’ (all my personal favourites), and many more.
In April 2023, their relationship ran its course. The split was amicable due to the differences in personalities and sheer pressure of fame. Ultimately, the six years they both shared stand as one of her most successful and cherished relationships. It was a safe haven for Taylor, especially during one of her most challenging periods, proving that despite her track record on short-lived relationships, she could maintain a genuine, long-term love. A love shared immensely that led the chapter to end on a genuinely peaceful note, free of drama.
This ain’t for the best
My reputation’s never been worse, so
You must like me for me
~ ‘Delicate’ by Taylor Swift ~
- Matty Healy
The brief 2023 fling with Matty Healy from The 1975 band. Their connection goes all the way back to 2014, when they were spotted wearing each other’s merchandise. However, Matty later clarified that their relationship at that time was “all fake”. Fast forward to the year 2023, the two reconnected following Taylor’s breakup with Joe Alwyn. It was rumoured that it was Jack Antonoff, Taylor’s long-term musical collaborator and close friend, who reunited them.
Their romance was quickly met with widespread backlash due to Matty Healy’s controversial reputation. This situation was deeply portrayed in her 2024 album, The Tortured Poets Department (TTPD). This included tracks like ‘But Daddy I Love Him’, ‘I Can Fix Him (No Really I Can)’ and ‘The Tortured Poets Department’, exploring her intense, immediate attraction and public disapproval of her relationship.
Then came her diss track, ‘The Smallest Man Who Ever Lived’, where Taylor suggests that she was ghosted. In its entirety, the relationship – or rather situationship – itself was brief, lasting only a few weeks. Their split reportedly was due to the immense pressure, personality incompatibility and clashes in their busy schedules.
You’ll slide into inboxes and slip through the bars
You crashed my party and your rental car
You said normal girls were boring
But you were gone by the morning
You kicked out the stage lights but you’re still performing
~ ‘The Smallest Man Who Ever Lived’ by Taylor Swift ~
Taylor Swift and Matty Healy at the Universal Music Brits Party
- Travis Kelce (finally!)
Last, but certainly not least, Taylor is currently engaged to Kansas City Chiefs player, Travis Kelce. Previously, Taylor had only dated actors and fellow musicians, but never an athlete; it was admittedly a nice change of pace.
In July 2023, Travis attended Taylor’s Era’s Tour show at Arrowhead Stadium, where the football player found himself crushing on the singer. On his ‘New Heights’ podcast, co-hosted by his brother, Jason Kelce, Travis revealed he attempted to meet Taylor and pass her a friendship bracelet after the show but was unsuccessful. This marked the start of a movie-worthy love story!
The two dated in secret, getting to know one another, before Taylor attended a Chiefs game two months later, which would soon become a habit for the remainder of the NFL season. Similarly, Travis became a regular face in her tour crowds, supporting her at various shows. He even made an on-stage appearance, right before The Tortured Poets Department set (the very album where Taylor had written two songs for him; ‘The Alchemy’ and ‘So High School’).
“No one’s ever had me, not like you
Truth, dare, spin bottles
You know how to ball
I know Aristotle”
~ ‘So High School’ by Taylor Swift ~
Taylor cheering Travis on at the Chiefs vs Chicago Bears game
Taylor Swift and Travis Kelce on stage at The Era’s Tour
In August 2025, following Taylor’s announcement of her upcoming album ‘The Life of a Showgirl’ on the Kelce brothers’ podcast, Travis knelt to the ground, pulled out a ring and asked Taylor to marry him. Their engagement has sparked a new era for both Taylor and her fans; an era filled with hope, stability and the kind of love Taylor has always written of, but never truly captured.
What’s so beautiful about her relationship with Travis is how intentional it’s been. Travis was never afraid of showcasing his love to her publicly. They openly supported one another, and one’s spotlight never outshined the other. For the first time, Taylor’s love life isn’t tangled in immature phone calls, a lack of commitment, kisses in secrecy or a fragile career-relationship imbalance; it is rooted in love and mutual respect. Travis doesn’t dim her light, but rather somehow brightens it! And judging by the smiles on their faces, this is simply a new chapter in a love story, and Taylor did, in fact, say yes.
“Where’s the trophy?
He just comes running over to me
Touch down, call the amateurs
And cut em’ from the team”
~ ‘The Alchemy’ by Taylor Swift ~
Travis Kelce and Taylor Swift announce their engagement
Taylor Swift’s engagement ring
Lessons In Love
For years, critics have pinned Taylor as the problem in her past failed relationships, simply because her dating history was so extensive. But instead of letting that define her, Taylor never stopped searching for the love she’s dreamed of, instead learning, growing and coming out of each relationship stronger than ever.
In Travis, it’s safe to say Taylor has found her other half, and we certainly can’t wait to see what music this love story will bring!
Written By: Ashley Anne Danker and Felicia Kong
Edited By: Sarah Wong
