Top 10 Men Taylor Swift Has Dated—Ranked

Top 10 Men Taylor Swift Has Dated—Ranked

Taylor Swift’s love life has been a subject of intrigue and fascination for fans and media alike. Her relationships have sparked countless songs, some iconic and others introspective, offering glimpses into her emotional world. Here’s a look at ten of her most talked-about romances, each bringing its own unique chapter to her story.

1. Joe Jonas

Back in 2008, teenage Taylor Swift was on top of the world — and so was Joe Jonas. The two young stars became one of Hollywood’s cutest couples, capturing the hearts of fans who loved seeing their fairytale unfold. But that dream came crashing down with a now-infamous 27-second breakup call that became pop-culture legend.

Instead of wallowing, Taylor did what she does best — she wrote about it. Songs like “Forever & Always” gave listeners a peek into her heartbreak, and fans instantly sided with her. Joe later admitted he was “immature” about the whole thing, showing that even celebrities have growing pains in young love.

Years later, both stars have long since moved on, but this relationship will forever be remembered as Taylor’s first high-profile heartbreak — the one that launched a thousand breakup anthems.

2. Taylor Lautner

Not many people can say they’ve dated someone who shares their first name, but Taylor Swift and Taylor Lautner made it work — at least for a little while. The two met while filming Valentine’s Day in 2009, and fans were immediately obsessed with their adorably shy chemistry both on and off-screen.

Their relationship was short-lived but sweet, and Lautner later revealed he was the one left heartbroken when things ended. Taylor Swift immortalized the romance with her hit “Back to December,” a rare apology song where she owned up to ending things too soon.

The best part? There’s no bad blood between them. Lautner recently appeared in Swift’s Speak Now (Taylor’s Version) music video, proving that sometimes young love really can turn into lifelong respect — and maybe even friendship.

3. John Mayer

Few relationships have sparked as much conversation as Taylor’s brief but intense connection with John Mayer. Their age difference — she was 19 and he was 32 — raised eyebrows, but it also fueled one of her most emotional songs ever: “Dear John.”

The track is a haunting reflection of feeling manipulated and discarded by someone older and more experienced. Mayer didn’t take kindly to it, calling the song “humiliating,” but Swift stood by her artistry, saying she writes about her feelings — not to hurt anyone, but to heal.

While the relationship was turbulent, it taught Taylor valuable lessons about self-worth and boundaries. Looking back, it’s clear this chapter was less about romance and more about growth, both as a person and as an artist.

4. Jake Gyllenhaal

When Taylor and Jake Gyllenhaal dated in 2010, it seemed like the perfect Hollywood pairing. She was America’s sweetheart, and he was the charming indie actor — but behind the smiles and coffee runs lay a relationship that burned bright and fizzled fast.

Their brief romance inspired several songs from Red, including “All Too Well,” arguably one of her most acclaimed works. Fans dissected the lyrics — the scarf, the age gap, the emotional distance — and built a modern myth around their time together.

More than a decade later, when Taylor released Red (Taylor’s Version), the 10-minute version of “All Too Well” reignited public fascination. It wasn’t just about Jake anymore — it was about every heartbreak that feels unfinished, every goodbye that still stings.

5. Harry Styles

For a few glorious months in 2012, the world’s most famous pop stars were a couple. Taylor Swift and Harry Styles’ relationship was a media frenzy, with paparazzi chasing them through New York streets and fans on both sides rooting for “Haylor.”

Though their romance was short, it clearly left a mark. Taylor’s songs “Style” and “Out of the Woods” are believed to capture the highs and lows of their passionate connection — from their undeniable chemistry to the chaos that came with fame.

Both have since spoken fondly of each other, with Styles even praising her songwriting. It’s one of those relationships that feels frozen in time — two young icons whose brief spark became part of pop culture history.

6. Calvin Harris

In 2015, Taylor Swift and Calvin Harris were the “it” couple of the music world. He was the world’s highest-paid DJ; she was dominating pop charts — together, they were unstoppable.

Their relationship seemed refreshingly down-to-earth despite their fame. They shared sweet photos on Instagram, celebrated anniversaries, and even collaborated musically (though secretly) on “This Is What You Came For.”

Unfortunately, the romance eventually ran its course, and the breakup turned messy when writing credits came to light. Still, with time, both parties moved on gracefully. Looking back, their relationship was one of Taylor’s most adult and balanced — proof that even megastars can have love stories that feel surprisingly relatable.

7. Tom Hiddleston

The summer of 2016 belonged to Taylor Swift and Tom Hiddleston. After her breakup with Calvin Harris, the Loki actor swooped in — and their whirlwind romance became tabloid gold. Who could forget the “I ❤️ T.S.” tank top?

Their relationship was as dramatic as it was brief, spanning exotic vacations and red-carpet appearances that had fans questioning whether it was real or a PR stunt. Still, both seemed genuinely smitten for a while.

Ultimately, the spotlight became too intense, and the relationship fizzled after just a few months. Yet, it added another memorable chapter to Taylor’s love life — a story that reminded fans that sometimes chemistry and timing just don’t align.

8. Joe Alwyn

For six years, Taylor Swift’s romance with British actor Joe Alwyn was her most private — and arguably her most meaningful. The two met in 2016, and unlike her previous relationships, she kept this one away from the spotlight.

Their partnership inspired much of her Reputation, Lover, Folklore, and Evermore albums, marking a creative and emotional high point. Joe even co-wrote songs with her under the pseudonym William Bowery, proving their bond extended far beyond romance.

When news of their 2023 split broke, fans were heartbroken. It was clear this wasn’t a scandalous breakup — just two people quietly growing apart. Their love story may have ended, but it left behind some of Taylor’s most mature and introspective work.

9. Matty Healy

After her breakup with Joe Alwyn, Taylor’s brief reunion with The 1975 frontman Matty Healy shocked the internet. The two had been friends for years, and their chemistry quickly reignited in the spring of 2023.

Fans had mixed feelings — some loved the pairing, while others criticized Healy’s controversial persona. Regardless, the fling was fast, fiery, and short-lived, ending almost as quickly as it began.

Though their romance didn’t last, it symbolized Taylor stepping back into the dating world with confidence and boldness. It was messy, real, and very human — a reminder that even superstars sometimes date the wrong person before finding the right one.

10. Travis Kelce

In 2023, the world collectively cheered when Taylor Swift began dating Kansas City Chiefs star Travis Kelce. The NFL player had publicly shot his shot after attending her concert — and surprisingly, it worked.

Their relationship became a cultural moment, uniting Swifties and sports fans alike. From stadium appearances to sweet public displays of affection, the two proved that love doesn’t have to hide to be genuine.

Travis has been refreshingly open about his admiration for Taylor, calling her “the real deal,” and she’s been spotted cheering him on from the stands. Together, they’ve become America’s favorite couple — and maybe, just maybe, this could be Taylor’s endgame.