By Wonderwall.com Editors
8:00am PDT, Apr 20, 2024
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Taylor Swift's love life has been publicly dissected ever since she burst onto the country music scene back in 2006. In the years since, the singer has had very public romances, very private romances and everything in between. Her fans have always supported her relationships, but that's not to say they don't have their favorites…
In honor of the billionaire pop star's "The Tortured Poets Department" double album, which dropped on April 19, we're looking back at all the men the Grammy winner has loved and lost over the years — and ranking them from worst to best.
Keep reading to see where your favorites rank…
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No. 11: Matty Healy
Taylor Swift first sparked up a flirtation with Matty Healy in 2014, though she didn't start seeing the rocker until early 2023 — fresh off her split from long-term partner Joe Alwyn (more on him later). Fans were pleased that the pop star's romance with the controversial frontman of The 1975, who's known for his bad-boy antics, proved to be short-lived: Things between them ended on a sour note when Matty reportedly ghosted Taylor to pick up the European leg of his band's "At Their Very Best" tour in mid-2023.
No. 10: Jake Gyllenhaal
Give her back the scarf, Jake! Jake Gyllenhaal reportedly dumped Taylor Swift via text after about three months of dating back in 2010. The Oscar nominee, who's nearly a decade older than the pop star, reportedly struggled with their age difference and the harsh glare of the spotlight on their relationship. He reportedly inspired her gut-wrenching breakup anthem "All Too Well" — which is all you need to know about how this romance ran its course!
No. 9: John Mayer
Taylor Swift and John Mayer briefly dated in late 2009 and early 2010 when she was 19 and he was 32. She famously took aim at their age difference — and their unfair power dynamic — in her 2010 track "Dear John," singing, "I lived in your chess game, but you changed the rules every day."
She later belts in the chorus, "Dear John, I see it all now that you're gone. Don't you think I was too young to be messed with?"
We sure think so!
No. 8: Joe Alwyn
We'll admit it: We thought they were a match made in heaven! But apparently — as Taylor Swift would say — her relationship with Joe Alwyn turned out to be "a nightmare dressed like a daydream." The duo were first publicly linked in 2017 — well into their relationship. The pop star later explained that she and the English actor — who contributed to her "Folklore" and "Evermore" albums — "decided together we wanted our relationship to be private."
Years later, we learned the real reason why: Joe, who was rarely seen with Taylor in public, struggled with her life in the limelight.
"They had plenty in common and fell in love in a safe bubble while she was retreating from the world during [her] 'Reputation' [era]," a source told People magazine after the breakup. "Then the pandemic hit, and they were locked down together and able to continue growing their relationship in this insulated way. But he didn't really 'know' her yet outside of that bubble."
"Joe has struggled with Taylor's level of fame and the attention from the public," the source added. "The differences in their personalities have also become harder to ignore after years together. They've grown apart."
No. 7: Calvin Harris
It was her first long-term relationship: Taylor Swift dated Calvin Harris for more than a year in 2015 and 2016, prompting Swifties to wonder if the Scottish DJ could be "The One." But the couple called it quits after Taylor secretly collaborated with Calvin on the most popular song of his career: "This Is What You Came For." (Rihanna sings vocals on the track.) He was later forced to shoot down rumors that they split because he was "intimidated" by her career and success: "The only truth here is that a relationship came to an end and what remains is a huge amount of love and respect," he tweeted at the time. (Taylor re-tweeted his note.)
No. 6: Conor Kennedy
Taylor Swift memorably dated a Kennedy — Robert F. Kennedy's grandson Conor Kennedy — when she was 22 and he was 18 and still a high school student. During their three-month relationship, she dropped $4.9 million on a mansion near the Kennedy compound in Hyannis Port, Massachusetts. She reportedly banked $1 million in profit when she sold the property the following year after their whirlwind romance came to an end. So we guess it was worth it!
No. 5: Joe Jonas
Taylor Swift's first public romance? Joe Jonas! They dated for a few months in 2008 until he famously broke up with her in a 27-second phone call… and then quickly moved on with Camilla Belle, prompting rumors he cheated on the pop star with the actress.
Surprisingly, that wasn't the end of Taylor and Joe: In 2015, he said they'd become "friends" again, and in 2019, she said of their bad breakup, "We laugh about it now." Taylor also developed a friendship with Joe's now-ex-wife, Sophie Turner — a friendship the two women maintained after Sophie and Joe called it quits in 2023.
We'll always root for friendly exes! Speaking of which…
No. 4: Harry Styles
Taylor Swift and Harry Styles dated for a few months in late 2012 and early 2013 until their relationship imploded after they reportedly got into an argument while vacationing together in the Virgin Islands after the holidays. According to reports, she was looking for something serious and he just wasn't ready to settle down yet. Fair enough!
In the years since the breakup, it's become clear that there's no bad blood between them: Taylor and Harry were seen chatting, hugging and cheering each other on at both the 2021 and 2023 Grammys.
No. 3: Tom Hiddleston
It was the rebound romance no one saw coming: Taylor Swift was seen kissing Tom Hiddleston just weeks after she split from Calvin Harris in mid-2016, prompting questions about the timeline of the breakup and whether or not there was overlap between the two relationships. The pop star and the Marvel actor spent the summer traveling the world together and then abruptly called it quits that September — after he was photographed wearing an "I Heart T.S." T-shirt mere weeks into their relationship. At the time, Us Weekly reported that Tom had pursued Taylor hard and that things were simply moving too fast for her.
The following year, he had nothing but good things to say a bout her, telling GQ, "Taylor is an amazing woman. She's generous and kind and lovely, and we had the best time." He also insisted that their relationship was real and not a publicity stunt — as many Swifties suspected.
No. 2: Taylor Lautner
Taylor and Taylor. It just seemed perfect. Taylor Swift and Taylor Lautner fell for each other while playing teen lovers in the 2010 ensemble rom-com "Valentine's Day." They dated for three months during the fall of 2009 until she broke up with him. (Their split reportedly inspired her power ballad "Back to December," in which she shares her regret over ending a relationship.)
Since then, the Taylors have become close pals. (The pop star is friendly with the "Twilight" actor's wife too!) In 2023, he starred in her "I Can See You" music video and gushed of her on stage when she brought her "The Eras Tour" show to Kansas City, "I respect you so much. Not just for the singer you are, the songwriter, the performer — but truly for the human you are. You are gracious, humble, kind, and I'm honored to know you."
No. 1: Travis Kelce
No surprise here! Taylor Swift has never seemed happier — or more herself — than she has with Travis Kelce. The once uber-private pop star hasn't shied away from flaunting her romance with the professional football player in public. Whether they're kissing at the Super Bowl or dancing together at Coachella, it's clear that despite their different backgrounds, these two are simpatico. We love how much they've showed up for each other since they started dating in the summer of 2023 — she became a fixture at Kansas City Chiefs game and he became a regular at international stops on her globe-spanning "The Eras Tour." We ship it!
