Taylor Swift's romance retrospective: All the men she's loved and lost

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Since breaking onto the scene with her self-titled debut album in 2006, Taylor Swift has proven herself to be an incredible songwriter — especially when it comes to crafting hits about heartbreak. As her spotlight grew, so did the star power of her relationships. Join Wonderwall.com as we take a look back at Taylor’s romances, from a young Jonas brother to an Academy Award-nominated actor and beyond.

Keep reading to see them all…

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Who could forget the relationship that ended in a savage 27-second phone call? Not us! Back in 2008, Taylor Swift dated Disney star and Jonas Brothers member Joe Jonas for three months. While their romance may have been short-lived, the fallout lasted much longer, as Taylor ended up penning four track allegedly inspired by Joe — “Forever & Always,” “Last Kiss,” “Better Than Revenge” (which was allegedly about actress Camilla Belle, whom Joe began dating shortly after their split) and “Mr. Perfectly Fine” — for her second studio album, “Fearless,” which went on to earn her her first-ever Grammy. The former teen pop stars are now on good terms: In 2015, Joe said they’d become “friends” again, and in Taylor’s 2020 track “invisible string,” she mentions that she sent Joe and his wife, actress Sophie Turner, a gift for their newborn baby.

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In 2009, Taylor Swift and Lucas Till were an item for a few short months. The actor — who met Taylor on the set of “Hannah Montana: The Movie” (she made a cameo) — starred in Taylor’s “You Belong With Me” music video as her love interest.

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We all felt the pain of Taylor Swift’s split from “Twilight Saga” actor Taylor Lautner when we listened to her heartfelt apology track “Back to December” off her 2010 album, “Speak Now.” Taylor and Taylor — aptly dubbed “Taylor Squared” by fans — met while filming the rom-com “Valentine’s Day,” in which they portrayed an adorable high school couple. They reportedly dated for three months during the fall of 2009.

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Shocked to find out that these two may have been an item? Yeah, so were we! For less than a month in the spring of 2010, Taylor Swift allegedly dated “Glee” star Cory Monteith, who died from an accidental drug overdose three years later. She reportedly wrote the song “Mine” off her 2010 album, “Speak Now,” about the Canadian actor. Aw!

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“Dear, John — Don’t you think 19’s too young to be played by your dark twisted games when I loved you so?” Yikes. In late 2009 and early 2010, a then-19-year-old Taylor Swift quietly dated a then-32-year-old John Mayer, with whom she’d collaborated on the 2009 track “Half of My Heart.” In addition to penning the 2010 song “Dear John” about him, Tay’s tracks “The Story of Us” and “Superman” — from her 2010 album “Speak Now” — were also reportedly inspired by the Grammy winning singer-songwriter who later told Rolling Stone he “didn’t deserve” to be called out in “Dear John,” branding it “cheap songwriting” and “a really lousy thing to do.”

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By now, you’re probably pretty well-versed in the Jake Gyllenhaal-versus-Taylor Swift drama (if not, we suggest you watch Tay’s “All Too Well” short film that dropped in 2021). Taylor and her former movie star beau dated for three months in late 2010 and their messy breakup spawned several scathing tracks in addition to “All Too Well” — “We Are Never Getting Back Together,” “State of Grace” and “Red,” all of which are on her 2012 album, “Red.” As for the reported cause of their split? The age gap was too big — Jake, who was 29 at the time, apparently called it quits with Taylor, who was 20 at the time, via text.

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It’s true, Taylor Swift once romanced a Kennedy! In 2012, the Grammy winner made headlines when she was spotted spending lots of time with Conor Kennedy, the grandson of Robert F. Kennedy who’s four years her junior (she was 22 at the time) and was still a high school student at the time. During their three-month relationship, Taylor purchased a $4.9 million home near the Kennedy estate in Hyannis Port, Massachusetts, which she sold the following year. Conor was the alleged inspiration for songs including “Begin Again,” “Everything Has Changed” and “Starlight” off her 2012 album, “Red.”

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Back in 2015, Taylor Swift found herself involved with perhaps one of Hollywood’s most sought-after heartthrobs: Former boy band member-turned-acclaimed solo artist-turned-movie star Harry Styles. Taylor publicly dated the “Watermelon Sugar” in late 2012, with the romance imploding after they reportedly got into an argument during the holidays. Taylor’s songs “Out of the Woods” and “cardigan” are allegedly about the English crooner, as is the oh-so-subtle track “Style” off her 2014 album, “1989.”

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Taylor Swift and Scottish DJ Calvin Harris sent the rumor mill into a frenzy when they were first photographed together in early 2015. They confirmed their romance a few months later when they attended the 2015 Billboard Music Awards together. But their love wasn’t meant to last — Taylor and the “Feel So Close” hitmaker — with whom she secretly collaborated to write his hit track “This Is What You Came For” featuring Rihanna — headed to splitsville in 2016 after more than a year of dating. Apparently, the track “I Forgot That You Existed” from Taylor’s 2019 album, “Lover,” was inspired by Calvin.

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Raise your hand if you too remember this whirlwind romance! It all started at the 2016 Met Gala, which, if you recall, is where Taylor Swift and Tom Hiddleston were spotted dancing together in a viral video. The pop star and her Marvel Cinematic Universe beau — together referred to as “Hiddleswift” — confirmed romance rumors when they were seen kissing on a Rhode Island beach next to her summer home weeks later following her split from Calvin Harris. Alas, all good things (and short flings) must come to an end: By early September, it was over for Tay and Tom after a summer spent traveling together to his native U.K., Italy, Australia and more. She reportedly wrote the “1989” track “Getaway Car” about quickly getting into a relationship with Tom after ending things with Calvin.

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It seems Taylor Swift has found her forever love! In 2017, she embarked on her longest relationship to date when she fell for “The Favourite” actor Joe Alwyn. In a departure from her previous relationships, Taylor and Joe “decided together we wanted our relationship to be private,” she explained in her 2020 documentary, “Miss Americana.” Later that year, she told Paul McCartney in a joint Rolling Stone interview, “I think that in knowing [Joe] and being in the relationship I am in now, I have definitely made decisions that have made my life feel more like a real life and less like just a storyline to be commented on in tabloids.” The “reputation” singer-songwriter has written countless tracks about her leading man, including “Call It What You Want,” “Lover” and “Gold Rush.” Joe even co-wrote some of Taylor’s songs on her albums “folklore” and “evermore” under the pseudonym William Bowery. We love their love! 














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