HomeEntertainmentWho has been Taylor Swift's boyfriend? and dating history!

Who has been Taylor Swift’s boyfriend? and dating history!

Here’s what we know about Taylor Swift’s boyfriend. For several years now, as we’ve passionately sung along with Taylor Swift’s breakup songs that strangely mirror our own life experiences, this artist, who transitioned from country to pop, has been romantically involved with numerous Hollywood leading men.

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The ‘Midnights’ artist has found herself connected to both musicians and actors, showcasing a knack for transforming her ended romances into songs. Taylor has most recently been rumored to be seeing Travis Kelce. An NFL player for the Kansas City Chiefs who has dated Taylor Swift. From Jake Gyllenhaal to John Mayer, every fortunate man has been in a dating relationship with Taylor Swift since she rose to fame with her first album, Fearless.

Who is Taylor Swift’s boyfriend?

Taylor Swift's boyfriends

Here’s a list, in order, of all the men Taylor Swift has dated. Inquiring about her musical tracks that explore the theme of love.

Joe Jonas and Taylor Swift

Taylor became romantically involved with the ex-boyfriend of the Jonas Brothers, who later took the spotlight as the leading figure of DNCE, from July through October 2008. Marking her inaugural split that was made public, it turned particularly harsh when Joe chose to end things via a brief 27-second call. The anguish of this split is believed to have inspired Taylor’s tracks “Last Kiss” and “Forever and Always” with a reflection on their fleeting affair, whereas “Holy Ground” offers a more upbeat view of their former chemistry later on. Eventually, Jonas found love with Sophie Turner, culminating in their decision to part ways in 2023.

Lucas Till and Taylor Swift

Taylor Swift’s boyfriend Lucas Till shared a brief romantic connection in 2009, following his appearance as her neighbour in the music video for “You Belong With Me.”. Lucas opened up about their short-lived relationship, expressing that they ultimately found they were more compatible as friends than as romantic partners.

“Initially, we did date for a short period. However, there wasn’t any conflict since we both were exceptionally amiable,” he shared with MTV. “Our liking for each other was strong… [But] for a relationship to progress, usually, it involves disagreements and then reconciliations, which adds passion. For us, my fondness for her was more platonic. That’s principally why it didn’t work out.”

Drew Dunlap and Taylor Swift

“Drew, Taylor Swift’s boyfriend, served as the muse behind the track.” Tim McGraw.”Their bond dissolved due to his departure from university studies. Speaking to USA Today, Taylor shared, “He purchased my album [Taylor Swift] and expressed his deep appreciation for it, which was touching. Nevertheless, his new girlfriend does not share the same enthusiasm.” As he was embarking on his collegiate journey, she felt compelled to pen something that would serve as a memorable farewell.”

Taylor Lautner and Taylor Swift

The unforgettable fling between Taylor and Taylor back in 2009 remains a noteworthy story. Their paths crossed while portraying love interests in the high school drama depicted in the movie “Valentine’s Day.” The track “Back to December” by Taylor alludes to her former relationship with Taylor Lautner. In it, she reflects regretfully on a disheartening evening in December, expressing remorse through lyrics about his bronzed complexion and charming smile, following the night she ended things with him.

John Mayer and Taylor Swift

John Mayer was one of Taylor Swift’s boyfriends. “In a 2012 conversation with Rolling Stone, Mayer expressed his distress, stating, “It brought me down because I hadn’t earned that kind of treatment.”. ”Nowadays, I’m quite adept at holding myself responsible, and I can confidently say I did nothing to warrant such. For her to act in that manner was truly low.”

In a musical retort, Mayer introduced ‘Paper Dolls’ in his 2013 Paradise Valley album. He vocalizes, “Wasn’t I too young to be played with? The girl wearing the dress shed tears all the way home, I ought to have realised.”

Jake Gyllenhaal  and Taylor Swift

It’s rumored that Jake Gyllenhaal shelled out around $160,000 for a private jet to fly her over for a romantic rendezvous, only to later end things via a text message. Songs like “We Are Never Ever Getting Back Together,” “I Almost Do,” “State Grace,” and “All Too Well” in both the original and lengthy 10-minute versions, “Red,” and “The Moment I Knew” are speculated to draw inspiration from their relationship.

Furthermore, tracks that were previously unreleased, including “Better Man,” “Babe,” and “I Bet You Think About Me,” which made it onto the re-recorded album of Red, are also believed to be reflective of their time together.

Additionally, their relationship gets a mention in the “Coney Island” track from the album Evermore, particularly through the lyrics, “Were you standing in the hallway with a big cake, happy birthday?” hinting at Jake’s absence from Taylor’s 21st birthday celebration—a detail that’s also been touched upon in the songs “The Moment I Knew” and the original 10-minute cut of “All Too Well.”.

Cory Monteith  and Taylor Swift

Cory Monteith was one of Taylor Swift’s boyfriends. Despite never openly confirming their relationship, Taylor and the star from Glee have been spotted together several times. Whenever Taylor was questioned about their past relationship during an appearance on The Ellen DeGeneres Show, it was evident she became embarrassed. On the unfortunate day Cory passed away in July 2013, Taylor’s reaction was to post a tweet saying, “At a loss for words. And for the most heartbreaking reason.”

Adam Young and Taylor Swift

“The track ‘Enchanted’ narrates the connection with Adam Young from Owl City. Though there was never a romantic relationship between them, he had expressed his feelings towards her.”

Zac Efron and Taylor Swift

A former idol from Disney’s High School Musical, Zac, had been making our hearts flutter long before his brief encounter with Tay. It’s rumored that they began seeing each other for a handful of months while on the promotional tour for their film, The Lorax. Nonetheless, both parties have dismissed any claims of romance.

In an amusing twist, the duo decided to address the speculation head-on by performing a song. They crafted a parody of Foster the People’s hit “Pumped Up Kicks” on The Ellen DeGeneres Show, humorously quashing the dating rumors. Despite their denials, we’re left to hold on to our fantasies.

Chord Overstreet  and Taylor Swift

Chord Overstreet was one of Taylor Swift’s boyfriends. “It seems that Taylor and Chord were only seen together during a solitary outing, yet, considering there are photographs documenting the occasion, he’s unavoidably included in the enumeration.

Eddie Redmayne and Taylor Swift

Eddie Redmayne was one of Taylor Swift’s boyfriends in the past. Gossip has it that the romance between Taylor and Eddie bloomed during her auditions for the role of Eponine in Les Misérables. They frequently appeared together across New York during the auditioning period. Sadly, Eddie’s alluring green eyes and speckled cheeks weren’t sufficient to inspire a dedicated song.

Harry Styles and Taylor Swift

One of the most controversial relationships Taylor has experienced to this day involves only being together for a brief period. Despite this, they both wore necklaces shaped like paper planes, took leisurely walks in Central Park, shared a kiss in Times Square during New Year’s Eve, and were even involved in a snowmobile crash.

The song “I Knew You Were Trouble” points directly at the One Direction star. Within Taylor’s album “1989,” there are numerous subtle nods towards Harry Styles. This is particularly evident in “Out of the Woods,” which includes lyrics hinting at their December affair and the mishap they experienced, and “Style,” which, by its name, makes the connection quite apparent.

Conor Kennedy  and Taylor Swift

During the 2012 summer months, Taylor entered into a relationship with Conor Kennedy, a descendant of Robert F. Kennedy. The pair faced scrutiny due to their age gap, with Taylor being 22 and Conor 18 at the time. Amid their relationship, Taylor went as far as buying a residence close to the Kennedy family’s estate in Hyannis Port, Massachusetts.

Tensions began to rise when Conor’s relatives claimed Taylor interrupted the wedding of Conor’s cousin Kyle in August, despite her representatives’ denial of such accusations. It seemed the relationship took a hit from these events. The song “Begin Again” is widely believed to be about Conor, particularly highlighted by the line, “I think it’s strange that you think I’m funny ’cause he never did,” suggesting a new appreciation she found in Conor that was lacking in her previous relationship.

Calvin Harris and Taylor Swift

The most frequently documented couple in the media is Taylor and Harris, who have a lengthy love affair. They were often seen together at glamorous events and would share pictures on their online profiles. It is widely believed that Calvin was the one who desired the separation.

Although neither party has publicly addressed the issue, it is believed that Calvin served as the inspiration for Taylor’s number-one single “We Are Never Ever Ever Getting Back Together.” Despite this, a solid portion of Swift’s followers are convinced the song references Gyllenhaal.

Tom Hiddleston and Taylor Swift

The romance between Tom Hiddleston and Taylor Swift’s boyfriend, affectionately dubbed Hiddleswift, was a love affair that captivated people worldwide. Their relationship blossomed in New York, before embarking on a global tour that included stops in Rhode Island, Italy, Australia, and England, among others.

However, as the saying goes, nothing lasts forever. Merely two months after Hiddleston was seen wearing a t-shirt proclaiming ‘I Heart T.S.’, the pair decided to end their relationship.

Travis Kelce and Taylor Swift

Travis Kelce was one of Taylor Swift’s boyfriends. At 33, Kelce first disclosed his interest in Taylor during an episode of his podcast, New Heights, sharing that he crafted a version of the Eras Tour friendship bracelets, incorporating his contact number for her.

Following this revelation, the duo has since confirmed their relationship status. Taylor has been spotted at several of Travis’s matches, including the grand spectacle of the 2024 Super Bowl, and they’ve even been seen interlocking hands in the presence of paparazzi.

Joe Alwyn and Taylor Swift

Joe Alwyn was her ex-boyfriend of Taylor Swift, and their relationship stayed mostly under wraps. Their first public sighting was in 2017, when they were seen sipping coffee on a Nashville balcony, They remained together for six years until reports in April 2023 suggested they parted ways a few weeks prior.

The track ‘…Ready for It?’ has left fans torn, debating if it’s about Alwyn or Swift’s previous romantic interest, Harry Styles. BuzzFeed noted Swift seems to have confirmed via liking a Tumblr post that analyzed the lyrics, indicating they are indeed about Alwyn. Another song, ‘Gorgeous’, is unequivocally about him, with the words: “You make me so happy, it turns back to sad.”

Listeners have also interpreted a song from her album Reputation, ‘Dress’, as an allusion to her initial encounter with Alwyn, with lyrics hinting at a meeting between two lovers when one had bleached hair. Swift was sporting bleached hair at the Met Gala in 2016, sparking speculation that’s where the two first met.

Swift and Alwyn even worked jointly on her quarantine albums, Folklore and Evermore, where Alwyn is listed under the pseudonym “William Bowery.” Swift revealed during her Folklore: The Long Pond Studio Sessions film, saying, “I was like, ‘Hey, this might end up being awkward, we might end up hating this, [but] since we’re stuck in quarantine with nothing else to do, should we give songwriting together a try?’”

In 2019, whispers of engagement (and even marriage) began circulating when Swift’s album Lover hinted at matrimony, yet neither confirmed nor denied these speculations. In early 2022, Alwyn addressed the engagement buzz with a cryptic answer during an interview with the Wall Street Journal, stating, “If I had a pound for every time I think I’ve been told I’ve been engaged, then I’d have a lot of pound coins. I mean, the truth is, if the answer was yes, I wouldn’t say, and if the answer was no, I wouldn’t say.”

However, in April 2023, it was confirmed that they had peacefully ended their relationship. A source told ET it was “not dramatic” and that “the relationship had simply reached its natural conclusion. It’s why [Alwyn] hasn’t made appearances at any shows.” Marking what Swift would deem the end of an era.

Following this, Swift unveiled a new breakup anthem titled ‘You’re Losing Me’, which captures the dissolution of their bond in her articulate style. The song intimates the relationship that had naturally concluded, with the man in the narrative (believed to be Alwyn) expressing no desire for marriage. “And I wouldn’t marry me either, a pathological people-pleaser who only wanted you to see her,” she vocalizes.

Matty Healy and Taylor Swift

Following her split from Joe Alwyn after six years, Taylor seemed to easily move into a new relationship with Matty Healy. On May 3, The Sun initially broke the news about the relationship, hinting that Healy would show up at Taylor’s shows in Nashville as confirmation that their relationship was genuine.

“It’s still very early on, but everything feels correct. They did have a brief fling almost a decade ago, but the timing was off,” an insider disclosed to the publication. “Taylor and Joe ended things in February, ensuring there was no overlap.”

On May 5, sightings of Healy at Swift’s Nashville concert surfaced. He was present at all her performances in the city, even joining Phoebe Bridgers, the opening act for Swift, on stage. By May 6, they were spotted together in a vehicle, and by May 8, Entertainment Tonight announced that Swift’s producer, Jack Antonoff, had introduced the pair.

By May 11, the duo was reportedly seen clasping hands in New York, and on May 15, Healy made an appearance at Taylor’s local show in Philadelphia, with her dad, Scott Swift, by his side. The relationship was stamped as ‘official’ after they were observed leaving a party at Electric Lady Studios in New York City’s West Village, hand-in-hand, with Healy’s hand resting on Taylor’s lower back.

Swift’s selection of Healy has baffled fans, especially due to his history of controversy as the lead singer of the rock band The 1975. Swift, however, seems to be completely enamored of the situation.

Expressing her contentment to her fans at Gillette Stadium in Foxborough, Massachusetts, during her Eras Tour on May 21, she confided, “I kind of feel like telling you, I don’t know, I’ve just never been this happy in my life in all aspects of my life ever before. “And I just want to thank you for being a part of that. It’s not only about the tour. My life just really feels like it’s fallen into place.”

Abubakar is a writer and digital marketing expert. Who has founded multiple blogs and successful businesses in the fields of digital marketing, software development. A full-service digital media agency that partners with clients to boost their business outcomes.

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