No one writes a breakup song better than Taylor Swift — just ask Jake Gyllenhaal.
The “I Knew You Were Trouble” singer has been known to share all of the highs and lows of each relationship through her lyrics, leaving fans trying to sleuth out which ex-boyfriend inspired which songs.
Following the re-recording and re-releasing of her past albums like “Fearless” and “Red,” her past lovers have been making headlines again, too.
Check out Swift’s dating history below.
While their relationship in 2008 only lasted a couple of months, Taylor used the experience — including Jonas breaking up with her during a 25-second phone call — as inspiration for her second album, “Fearless.”
Songs such as “Forever & Always,” “Last Kiss,” “Better Than Revenge” and “Mr. Perfectly Fine” were all written about the DNCE singer. She later went on to win her first Grammy for the album.
“You might think I’d bring up Joe, that guy who broke up with me on the phone. But I’m not going to mention him in my monologue. Hey, Joe! I’m doing really well and I’m hosting ‘SNL’ — but I’m not going to write about that in my monologue,” sang Swift during her monologue the first time she hosted “Saturday Night Live” back in 2009.
Whether it was due to time — or the Grammy — the two seem to be on good terms as Jonas celebrated with Swift after her “SNL” appearance this past week.
The pair co-starred in Swift’s “You Belong With Me” music video back in 2009, but they met on the set of “Hannah Montana: The Movie,” in which Swift had a small cameo.
The pair split up months later saying they were better off being just friends.
Popularly known as “Taylor Squared,” the couple met while filming “Valentines Day” where they played high-school love interests.
It’s rumored that Lautner was more into Swift than she was into him, resulting in their breakup. Swift allegedly wrote “Back to December” about their romance where she seemingly tried to apologize to the “Twilight” star.
“You gave me roses, and I left them there to die / So this is me swallowing my pride, standing in front of you saying I’m sorry for that night,” wrote Swift in “Back to December.” “You gave me all of your love and all I gave you was goodbye”
In a response to the song, Lautner later said, “That’s just what she does.” Ouch.
The late “Glee” star and Swift only dated for about a month, but he still earned a sweet love song from the singer. It’s been alleged the song “Mine,” about a sweet boy she barely knows, is about Monteith.
Dear John, how could you forget this one?
The two dated for just a couple months after collaborating on “Half of My Heart.” Swift, who was 20, later called the “Gravity” singer, then 32, out in a song titled “Dear John”.
“Dear John, I see it all now, it was wrong / don’t you think 19 is too young to be played by your dark twisted games,” Swift sang on the track.
Mayer later responded to the song in an interview with Rolling Stone, stating, “I will say as a songwriter that I think it’s kind of cheap songwriting.”
Do you remember it “All Too Well” now, Jake?
Even though they only dated for three months in 2010, Swift had a lot to say about the actor in her album “Red,” which she recently re-released — including a scathing 10-minute version of “All Too Well,” a song about the couple’s breakup.
It’s also said that he inspired the songs, “We Are Never Getting Back Together,” “State of Grace,” and “The Moment I Knew.”
At the time Swift, 20, was blindsided when Gyllenhaal, 29, broke up with her via text, claiming the age gap was too much for the “Brokeback Mountain” actor.
Swift also recently released a short film to “All Too Well” that shows the timeline of the couple’s romance.
Swift dated Robert F. Kennedy’s grandson, Conor Kennedy, for a few short months back in 2012.
The unlikely duo did raise a couple of eyebrows given their respective ages at the time — Swift being 22 and Kennedy just 18.
Swift was a longtime fan of the Kennedys even before meeting Conor. She even wrote a song about Robert [Bobby] Kennedy and his wife Ethel’s courtship called “Starlight.”
Known as “Haylor,” the pair made their first public appearance in December of 2012 going for a stroll in Central Park.
“Swifties” and “Directioners” at the time went crazy about the new romance, but the excitement was short-lived, and the couple broke up after 3 months.
That same year Taylor seemingly lobbed a shot at Styles — sitting in the crowd during her performance of “We Are Never Getting Back Together” — at the Grammys, by singing the hit in an English accent.
The Scottish DJ and Singer sparked dating rumors after being photographed together in Whole Foods wearing color-coordinated outfits in March of 2015.
They then made things official by attending the Billboard Music Awards together in May where they got some PDA in for the cameras.
The couple dated for over a year, yet in March of 2016, Harris called things off in what pals described as a “brutal” split.
Taylor Swift and Tom Hiddleston met — and danced together — at the Met Gala in 2016.
Just one month later, pictures surfaced of the two kissing at the beach in Rhode Island, solidifying their relationship.
The couple, known as “Hiddleswift” caught everyone by surprise — including Swift.
It’s rumored she wrote the song “Getaway Car” about how bad she felt about getting into a new relationship so soon after her breakup with Harris.
Either way, the couple called it quits just a few months later.
Fast forward all the way to 2016 and Swift found herself in her longest — and most secretive — relationship yet.
She and actor Joe Alwyn met at the 2016 Met Gala and started dating a few months later, although news of their romance did not break until the following year.
“I was falling in love with someone who had a wonderfully normal, balanced life,” she said in her 2020 autobiographical documentary, “Miss Americana.”
“We decided together we wanted our relationship to be private. I was happy. But I wasn’t happy in the way I was trained to be happy. It was happiness without anyone else’s input. We were just happy.”
The pair split in April 2023 after more than six years together.
Weeks after her breakup from Alwyn made headlines, Swift was romantically linked to The 1975 frontman Matty Healy.
A source claimed to the Sun in May 2023 that the singers were in the “super-early” stages of dating but already “madly in love” with each other.
“Both Matty and Taylor have been touring over the past few weeks, so it’s been a lot of FaceTiming and texting, but she cannot wait to see him again,” the insider added, further claiming that Healy planned to attend Swift’s Eras Tour stop in Nashville.
Swift and Healy previously sparked dating rumors in late 2014 after being spotted wearing each other’s merchandise. He said at the time that they had “exchanged numbers” but later clarified that their relationship was “all fake.”
One month after news of their romance broke, TMZ reported that they had already split.
While NFL star Travis Kelce failed at shooting his shot with Swift at her Kansas City, Mo., Eras Tour stop in July 2023, he eventually won the long game.
Two months later, the Chiefs tight end was said to be “hanging out” with the Grammy winner and, after several hints and on-camera jokes, the two-time Super Bowl champion’s brother, Jason Kelce, jokingly confirmed the dating rumors were “100 percent true.”
“I think they’re doing great,” the Eagles center said before admitting he didn’t know what was happening between the two.
However, their relationship status was made pretty clear when Swift attended the Kansas City Chiefs’ game on Sept. 24.
She then became a staple at Chiefs games throughout the season, including rushing back from Tokyo to watch her beau and his team win Super Bowl LVIII in Las Vegas.
After the pair celebrated the championship, Swift hit the road again to continue her Eras Tour — but this time, Kelce had all the time in the world to follow her across the globe.
The tight end flew to Singapore and Sydney where joined Swifties in singing and dancing his heart out.
Following the conclusion of the Swift’s Singapore Eras Tour shows, the duo returned to the States briefly before enjoying some much-needed vacation time at a private estate in the Bahamas.
