Unbelievable Relationships: Taylor Swift’s Surprising Dating History

Unbelievable Relationships: Taylor Swift's Surprising Dating History

Taylor Swift has had relationships with ten other celebrities except Travis Kelce. Joe Jonas was the first name linked with the Cruel Summer singer. 

Taylor Swift isn’t just celebrated for her songwriting and singing. She’s also known for her high-profile relationships. She’s dated celebrities like Joe Jonas and John Mayer. Swift often channels her romantic experiences into her music. 

Through her songs, she openly shares her feelings about love and heartbreak. By turning personal sorrow into musical masterpieces, she resonates with fans worldwide.

Joe Jonas (2008)

When Taylor Swift was 18, her name was linked with fellow singer-songwriter Joe Jonas. However, we cannot definitively claim he was her first relationship.

Taylor Swift and Joe Jonas Relationship
Taylor Swift and Joe Jonas Relationship, Credit People

Taylor Swift often mentions her relationships in her music. In her self-titled debut album, she referenced Drew and Cory, though we don’t have any information about them. They might also be connected to her romantic life.

Joe Jonas was the first man with whom Taylor Swift had a publicly known relationship. However, despite many ambitions and efforts, this relationship did not last long. Taylor Swift and Joe Jonas met in July and broke up in October of the same year.

The root of their separation is unclear. However, according to Swift’s statement, their relationship ended after a 25-second phone call. This indicates that there was not much discussion between them about the relationship or the breakup.

During her appearance on The Ellen DeGeneres Show, Swift opened up about the breakup. “Someday, I’m gonna find somebody really, really, really great, who’s right for me… When I find that person that is right for me, he’ll be wonderful.” She added, “And when I look at that person, I’m not even gonna be able to remember the boy who broke up with me (Joe Jonas) over the phone in 25 seconds when I was 18,” she said.

Lucas Till (2009) 

Taylor Swift dated Lucas Till after his appearance in Swift’s “You Belong With Me” music video. Till played the singer’s love interest in the video, which contributed to their relationship. 

Taylor Swift and Lucas Till relationship
Taylor Swift and Lucas Till relationship; credit Girlfriend Magazine

According to Lucas Till, they dated for a few months and then ended the romantic relationship with mutual understanding. Lucas and Swift remain good friends after the breakup. 

In a statement during an interview with MTV, Till revealed, “We dated for a little but. But there was no friction because we were too nice. We just really both liked each other. Most relationships work out cause you get along and then you don’t and then you make up and it’s passionate, with us, I really just liked her as a friend. That’s the only reason that didn’t work out.” 

Taylor Lautner (2009) 

Taylor Swift and Lautner met while filming the romantic comedy “Valentine’s Day.” While playing opposite each other in the film, they became a real-life couple. However, this relationship also did not last long.

Taylor Lautner and Taylor Swift relationship
Swift and Taylor Lautner; credit people

They dated for about two months, from October to December, and were spotted together at many events, including Swift’s concerts and award shows.

Taylor Swift wrote the song “Back to December,” which is widely believed to be about her relationship with Lautner. The song, released in October 2010, expresses regret and apologies for how she handled their breakup, showing a rare moment of Swift taking responsibility for the end of a relationship.

Despite the breakup, both stars remained friends and spoke respectfully about each other.

John Mayer (2009 – 2010) 

“You Belong With Me” singer Taylor Swift also dated American singer-songwriter John Mayer. They first met professionally when Mayer invited Swift to collaborate on his song “Half of My Heart,” which was released in June 2009.

Taylor Swift and John Mayer Relationship
Swift and John Mayer Relationship; credit People

Speculation about a romantic relationship between Taylor and John grew as they made public appearances together, fueled further by their notable age difference: Swift was 19, and Mayer was 32, a gap of about 13 years.

After their relationship ended, Taylor Swift wrote and released the song “Dear John” on her 2010 album “Speak Now.” The song is widely believed to be about her relationship with Mayer and contains emotionally charged lyrics criticizing how Mayer treated her. Notable lines include, “Dear John, I see it all now that you’re gone / Don’t you think I was too young to be messed with?”

John Mayer disagreed with the song during an interview with Rolling Stone, stating that he felt humiliated by it.

Also read: Wiz Khalifa and Girlfriend Aimee Aguilar Are Expecting a Baby Together

Jake Gyllenhaal (2010) 

“Bad Blood” singer and Jake Gyllenhaal reportedly started dating in October 2010. They were first met at a dinner party by Gwyneth Paltrow. 

Jake Gyllenhaal and Taylor Swift
Jake and Swift; credit People

The couple was spotted together on several occasions after their first meeting at the party. They were caught enjoying weekends around Brooklyn, New York and some other places. However, this couple also has a huge age gap as Swift was just 20 and Jake was 29. One notable moment was when Gyllenhaal reportedly spent $160,000 to fly Swift on a private jet to spend Christmas with her family in Nashville. 

After a few months of dating, the couple reportedly broke up in January 2011. The breakup was said to be mutual, though Swift was reported to be heartbroken.

Taylor Swift’s 2012 album “Red” is widely believed to be inspired by her relationship with Gyllenhaal. The song “All Too Well,” in particular, is thought to chronicle their romance and breakup. 

Conor Kennedy (2012)

Taylor Swift also dated Robert F. Kennedy Jr.’s son, Conor Kennedy, adding to her list of exes. They reportedly began dating in the summer of 2012 after being introduced by mutual friends.

Taylor Swift and Conor Kennedy Relationship
Swift and Conor Kennedy Relationship; credit Instyle

Their relationship, bridging the worlds of a singer and a politician’s son, lasted only three months. During this time, they enjoyed each other’s company and were frequently seen together at various places and events, including the Kennedy Compound in Hyannis Port, Massachusetts, owned by Conor’s family.

Taylor Swift released the song “Begin Again” on her 2012 album “Red.” Although not explicitly mentioning Conor Kennedy, the song is widely interpreted to be inspired by their brief romance and alludes to Cape Cod, where they spent time together.

Media reports suggested that their relationship ended due to distance and their demanding schedules.

Harry Styles (2012 – 2013) 

Two pop stars linked up in November 2012 for a short duration relationship. They were first met through mutual friends in the music industry. However, Taylor and Harry quickly became romantically involved and their relationship sparked immediate interest from fans and the media. 

Taylor Swift and Harry Styles relationship
Swift and Harry Styles relationship; credit People

In December 2012, Swift and Styles were spotted together in New York City, where they were seen walking through Central Park and enjoying each other’s company. This public outing confirmed their relationship and intensified media coverage.

The relationship between Swift and Styles reportedly ended in early January 2013 after a brief but intense romance. The breakup was rumored to be due to conflicting schedules and the pressures of their high-profile careers.

Taylor Swift’s songs “Out of the Woods” and “Style,” released on her 2014 album “1989,” are widely known to be inspired by their love story. 

Calvin Harris (2015 – 2016) 

Taylor Swift and Calvin Harris came in a relationship after they met at the Elle Style Awards in February 2015. 

Calvin Harris and Taylor Swift Relationship
Calvin Harris and Taylor Swift; credit Koimoi

Swift and Harris often appeared together at public events and were seen showing affection towards each other, both in person and on social media. They shared photos of their vacations and special moments, which garnered attention from fans and the media.

In addition to their romantic relationship, they also collaborated professionally for the song “This is What You Came For.” 

After more than a year together, Taylor Swift and Calvin Harris announced their breakup in June 2016. Both parties released statements indicating that the split was amicable and that they would remain friends. However, they both unfollowed each other on social media after the breakup. 

Taylor Swift’s subsequent album, “Reputation,” released in November 2017, is believed to contain songs influenced by her relationship with Calvin Harris and its aftermath. 

Tom Hiddleston (2016) 

Swift met Avengers star Tom Hiddleston at the 2016 Met Gala when she was in a relationship with Harris. Three to four years after their first meeting, they started dating each other. 

Tom Hiddleston and Taylor Swift Relationship
Tom Hiddleston and Taylor Swift; credit Planet Radio

They were first seen together publicly in June 2016, shortly after Swift’s breakup with Calvin Harris. Photos of them cuddling and kissing on a beach in Rhode Island surfaced, marking their official debut as a couple.

Swift and Hiddleston’s relationship gained significant attention during Taylor Swift’s annual Fourth of July party at her Rhode Island home in 2016. Photos and videos of them dancing, kissing, and wearing matching “I ♥ TS” shirts went viral, sparking both amusement and curiosity.

Their relationship reportedly ended in September 2016 after just a few months of dating. Sources indicated that it had run its course due to the challenges of long-distance and conflicting schedules.

Joe Alwyn (2017 to 2023) 

Taylor Swift’s relationship with Joe Alwyn stands as the longest in the singer’s dating history. They first met in 2017, although some fans speculate it might have begun in 2016.

Joe Alwyn and Taylor Swift Relationship
Joe Alwyn and Taylor Swift; credit People

Swift and Alwyn have been notably private about their relationship, rarely appearing together at public events or sharing details on social media. They have chosen to keep a low profile.

Taylor Swift’s albums “Reputation” (2017), “Lover” (2019), and “Folklore” (2020) are believed to draw inspiration from her relationship with Joe Alwyn, marking the first time Swift openly expressed her feelings for her current boyfriend through her music.

However, in 2023, the relationship reportedly ended due to personal reasons.

Also read: Ex-WWE Superstar Steph De Lander Is Dating PCO 

Matty Healy (2023) 

Matty Healy was also romantically linked with Taylor Swift. However, he was not lucky enough to take their relationship long. Their relationship started during Swift’s Eras Tour when Healy went to watch her live. 

Matty Healy and Taylor Swift Relationship
Matty Healy and Taylor Swift Relationship; credit People

Matty and Swift were caught hanging out in places like Casa Cipriani in New York in May for a couple of weeks. However, they were separated at the start of June due to busy schedules. 

Travis Kelce (2023) 

Travis Kelce and Taylor Swift’s relationship had an unusual beginning that could be straight out of a movie. It all started when Kelce attended Swift’s Eras Tour in 2023 with a friendship bracelet in hand, intending to give it to her.

Travis Kelce and Taylor Swift relationship
Travis Kelce and Taylor Swift relationship

However, Kelce didn’t manage to present the bracelet to Swift during the event and returned without giving it to her. He later shared this incident on his podcast, which caught Swift’s attention.

After a few months, Kelce and Swift began a relationship. Their unique story of how they met added a touch of romance and intrigue to their journey together.

Also read: How Taylor Swift Manages to Perform in All Weather Conditions 

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