Learn About Her Dating History – Hollywood Life

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• Taylor Swift and Joe Alwyn began quietly dating in 2016 and news of their breakup made headlines in April 2023
• Joe Alwyn served as the inspiration for several albums of Taylor’s, including Reputation, Lover, Folklore, Evermore, and most recently, Midnights
• Reports that Taylor is dating the 1975 lead singer Matty Healy dropped in early May 2023
• Before Joe and Matty, Taylor dated other stars like Harry Styles, Joe Jonas, and more

Taylor Swift seemed to have met her match in Joe Alwyn; however, their relationship was reported to be over in April 2023 after six years that were spent almost entirely out of the spotlight.  The couple reportedly went through some “rough patches” before but recently decided that they “weren’t the right fit for one another” due to “differences in their personalities”, according to an insider for PEOPLE. Joe also reportedly struggled to deal with the global superstar’s level of fame. While the reported former couple had been shy about most details involving their relationship, fans know how happy Taylor and Joe were at one point thanks to the several songs that the “Anti-Hero” hitmaker wrote about their love.

Just one month after Taylor and Joe’s split made headlines, it was reported that the “Fearless” hitmaker is seeing The 1975  frontman, Matty Healy. Since then, he has been seen playing with Eras Tour opener Phoebe Bridgers on stage at and watching numerous of Taylor’s Eras Tour shows. Get the low down on their newly reported romance as well as Taylor’s dating history.

Matty Healy Romance

Taylor and Matty were first reported to be an item on May 3, 2023 by The Sun, and that was followed up by confirmation from an Entertainment Tonight source.“Taylor and Matty like each other,” the insider claimed “Taylor has a crush on Matty and they are having a good time hanging out. Matty also thinks Taylor is awesome and incredibly talented, too. They dated briefly in the past.” The musicians were first linked in 2014, but for a short amount of time.

Since then, then Matty and Taylor have seemingly not left each other’s sides. Matty attended all six of Taylor’s Nashville and Philadelphia Eras Tour shows, and was even seen getting along with Taylor’s longtime bestie Gigi Hadid from the V.I.P. tent at a show in Tennessee. He was then videotaped spending time with Taylor’s other pal, Blake Lively, and her two James, 7, and Inez, 6 at a Pennsylvania show. It appears that Matty even has the stamp of approval of Taylor’s parents, as he was also seen chatting it up with her dad at one of her shows.

@amimattingly

Replying to @charityxrae Matty Healy and Blake Lively talking at The Eras Tour Philly with Blake’s daughter Inez #taylorswift #theerastour #blakelively #inez #betty #mattyhealy #the1975 #taylorandmatty #theerastourphilly

♬ original sound – ami mattingly

Furthermore, the pair have been spotted out and about together several times since Matty’s first appearance in Nashville to support Taylor. The “Wildest Dreams” singer and “About You” hitmaker were reportedly photographed for the first time together on May 7 in a chauffeured black SUV in Nashville, which can be seen here. They were then spotted “cuddling and kissing” during a lunch rendezvous with their mutual producer friend, Jack Antonoff, at New York City’s Casa Cipriani on May 11. Taylor and Matty fueled rumors that they are collaborating on music together when they were seen leaving Electric Lady Studios in New York City on May 15 together. While they did not hold hands, Matty appeared to be guiding Taylor with his arm behind her back.

Neither Taylor nor Matty has confirmed their romance as of May 16, 2023.

Joe, a rising British actor, and the “Speak Now” songstress first crossed paths at the 2016 Met Gala, when Taylor was still with Irish DJ Calvin Harris. Taylor famously wrote about their first time seeing each other in her 2017 song, “Dress”, which is off her fiery album, Reputation. “They had plenty in common and fell in love in a safe bubble while she was retreating from the world during Reputation,” PEOPLE‘s source noted of the start of their love story. “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.”

Taylor and Joe were spotted in public together a handful of times throughout their romance, including on a Bahamas vacation during which they were photographed smooching in the gorgeous Caribbean waters. Their relationship mostly made headlines when they would make a rare comment about one another. In 2020, for instance, Taylor admitted she was “falling in love with someone who had a really wonderfully normal, balanced, grounded life” during her 2020 documentary, Taylor Swift: Miss Americana. She also told Paul McCartney her and Joe’s secret for maintaining a balanced and quiet life was all about trying to replicate “normalcy” any way they could. “Whether that’s deciding where to live, who to hang out with, when to not take a picture — the idea of privacy feels so strange to try to explain, but it’s really just trying to find bits of normalcy,” she said in their 2020 Rolling Stone cover story.

Taylor named Joe publicly for the first time in her 2020 documentary, Folklore: The Long Pond Studio Sessions. First, she confirmed that they worked on her song, “Exile”, together, on which he used a pseudonym: William Bowery. She then complimented his musical ability. “Joe plays piano beautifully, and he’s always just playing and making things up and kind of creating things,” she explained as she spoke about the song’s creation. “It was pretty obvious that it should be a duet ’cause he’s got such a low voice and it sounded really good sung down there and in that register.” In 2021, Taylor thanked Joe when accepting her third Grammy for Album Of The Year for Folklore and said he’s the first person she plays songs for. 

Taylor Swift’s Past Relationships

Tom Hiddleston

Before getting with Joe, Taylor dated English actor Tom Hiddleston for a few months following her split from Calvin Harris. They were first linked when they were photographed making out on the beach near Taylor’s Rhode Island beach house in June 2016. The pair were not afraid to be seen together, and on July 4, Tom rocked an “I [heart] T.S.” tee, as seen here. That same month, he denied that his and Taylor’s love was for show. “Well, um. How best to put this?” he told The Hollywood Reporter.  “The truth is that Taylor Swift and I are together, and we’re very happy. Thanks for asking.”

However, by August, the hot couple had reportedly gone their separate ways. They appear to be on good terms, per Tom’s 2017 interview with GQ in which he had nothing but good things to say about the Grammy Award-winning musician. “Taylor is an amazing woman,” he said. “She’s generous and kind and lovely, and we had the best time.”

Taylor’s song 2017 song “Getaway Car” is thought to be about Tom and how she used him to flee another relationship. “The ties were black, the lies were white, in shades of grey and candlelight, I wanted to leave him, I needed a reason,” she sings.

Calvin Harris

As noted above, Taylor was with the “Feel So Close” hitmaker before her summer fling with Tom. They dated for one year between 2015 and 2016. Around their one-year anniversary, Taylor called their romance “magical” while speaking to Vogue in April 2016. Unfortunately, they broke up a few months later.

Although they seemed to part ways on good terms, things changed when Taylor switched her pseudonym, Nils Sjoberg, to her real name on the writing credits for Calvin and Rihanna‘s viral hit, “This Is What You Came For”. He then took to Twitter to air his frustration about the ordeal. “I wrote the music, produced the song, arranged it and cut the vocals, though. And, initially, she wanted it kept secret, hence the pseudonym,” he wrote in a series of since-deleted tweets, per PEOPLE. “Hurtful to me at this point that her and her team would go so far out of their way to try and make ME look bad at this stage, though.”

“I figure if you’re happy in your new relationship you should focus on that instead of trying to tear your ex bf down for something to do,” he slammed in another tweet. “I know you’re off tour and you need someone new to try and bury like Katy [Perry] ETC but I’m not that guy, sorry. I won’t allow it.” Despite being upset, Calvin also complemented Taylor’s writing.

Harry Styles

Taylor reportedly began dating English musician Harry Styles (while he was still with One Direction) after they met at an award show in 2012. They dated for about a year. The exes are certainly on good terms, as they have been seen chatting with each other and cheering each other on at award shows on a few occasions. Taylor was notably filmed standing during Harry’s entire acceptance speech for the 2023 Grammy for Best Pop Vocal Album. Fans believe several of Taylor’s songs are written about the Don’t Worry Darling actor, including 2015’s “Style” and 2022’s “Maroon”.

📹 | Taylor Swift clapping for Harry Styles win for Best Pop Vocal Album at the #GRAMMYs pic.twitter.com/oVpR6xdjOd

— Taylor Swift News (@TSwiftNZ) February 6, 2023

Conor Kennedy

Taylor was linked to Conor Kennedy, Robert Kennedy‘s grandson, during the summer of 2012. Although she never confirmed their romance, she admitted her 2012 Red song, “Starlight”, was inspired by Conor’s grandparents after she saw an old photograph of them. “It immediately made me think of like how much fun they must have had that night,” Swift told The Wall Street Journal in Oct. 2012. “So I just kind of wrote that song from that place, not really knowing how they met or anything like that.”

Jake Gyllenhaal

It’s no secret that Taylor and Jake Gyllenhaal dated, as one of her most iconic songs of all time, “All Too Well”, is reportedly about the heartbreak resulting from the downfall of their relationship. The song has many parallels to their relationship and Jake’s life, such as their age gap (which was addressed in 2022’s “All Too Well (10 Minute Version) (Taylor’s Version) (From The Vault)”) and visiting her love interest’s sister’s house. Jake has a sister named Maggie. The 10-minute version of “All Too Well” also accuses the love interest of ditching her on her 21st birthday, which is when they were an item.

However, Taylor has never confirmed the song’s inspiration and Jake is sure the song has “nothing to do with” him. “It’s about her relationship with her fans,” the Los Angeles-born actor told Esquire in Feb. 2022. “It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”

Although their relationship was brief and never advanced out of 2012, it has made a lasting impact on Swifties.

John Mayer

John Mayer dated the “Willow” hitmaker between 2009 and 2010 after collaborating with her on his 2009 single “Half of My Heart”. He has since won the prize as Taylor’s most disliked boyfriend by her loyal fans due to the way he is reportedly portrayed in her songs about him. For instance, there is a song titled “Dear John” on her 2010 album, Speak Now. In the song, Taylor addressed their 12-year age gap and his supposed wrongdoing by sorrowfully belting, “I see it all now that you’re gone / Don’t you think I was too young to be messed with? / The girl in the dress cried the whole way home”.

John himself believes the lyrics are about him and even defended himself against the “humiliating” song in a 2012 interview with Rolling Stone. “It made me feel terrible. Because I didn’t deserve it,” he explained. “I’m pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do.” Taylor has never confirmed the inspiration behind the song.

John is also thought to be at the center of her 2022 Midnights bonus track, “Would’ve, Could’ve, Should’ve”, which sings about a regretted love when she was 19 years old — the age she was when she was seeing the Last Train Home hitmaker.

Taylor Lautner

The era of “Taylor Squared”. Taylor and the Twilight star dated for a few months in 2009 after they played a couple in the 2012 romantic comedy Valentine’s Day. The exes are on good terms, and Taylor and his wife (whose name is also Taylor) said in 2023 that they would love to attend the superstar’s in-demand Eras Tour.

Plus, during a deep conversation on the actor and his wife’s podcast in Feb. 2023, he mentioned his deepest regret involves his ex. “[My biggest regret is] probably the 2009 VMAs, when I presented the award to Taylor and was unaware that the Kanye [West] thing was not a skit,” he told his wife, referring to the viral moment during which the troubled rapper stormed the stage while Taylor was accepting her first-ever Video Music Awards win and said Beyonce deserved the trophy.

Lucas Till

Lucas Till starred in the Pennsylvania native’s 2009 music video for “You Belong With Me” and they dated afterward, but briefly. “There was no friction because we were too nice. We just really both liked each other,” Lucas recalled to MTV in 2009. “Most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”

Joe Jonas

Taylor and Joe Jonas were together for about three months in 2008. Taylor infamously revealed during an appearance on The Ellen DeGeneres Show that the Jonas Brothers member broke up with her in a 25-second phone call. “When I find that person who is right for me, he’ll be wonderful, and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she stated. She later confirmed the boy who dumped her over the phone was Joe while hosting Saturday Night Live in 2009. The situation inspired her 2008 Fearless song, “Forever & Always”.

Fortunately, Taylor and Joe are on great terms now. Fans believe she sang about their improved relationship in her 2020 song, “Invisible Strings,” from Folklore. “Cold was the steel of my axe to grind/ For the boys who broke my heart/ Now I send their babies presents,” she sings. Joe, of course, has two children now, so she very well may have sent him and his wife, Sophie Turner, presents. Sophie is also a huge Taylor fan, and she is not afraid to show it.

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